The 2 Day Board Meeting: Speed Dating, Texas Hold ‘Em, and Green Pants

Investors in Green Pants
Windsor Circle Investors Rocking the Green Pants

At Windsor Circle, we define team not by who is on the payroll or inside our four walls, but truly by everyone who is working to build the Center of the Retention Automation Universe.

This includes our employees, our service providers (attorneys, accountants, landlords, etc.), interns, and most certainly our investors.

We have worked hard to find investors who share our values, see the same opportunity that we do, and who could add far more than just their dollars to our efforts.

The Two Day Board Meeting…  What the?

Believe it or not, we hold a two-day board meeting every other quarter.  We do this because we want to unlock the collective experience and insights of a talented set of market makers, and feel that you can’t do that with an 3-hour board meeting where all you are doing is giving updates.

We do a financial call two weeks prior to the meeting to get all of the updates done, and to provide 2 weeks of time for the board to think about the data.

The board meeting itself is held onsite, spans two days, and is driven specifically by two main objectives:

  1. Strategic Thinking – We aim to make the board meeting itself a 4 hour conversation.  No board deck, no updates.  We did that in the financial call…  this is about collective thinking, problem solving and “strategery.”
  2. Team Building – We make certain that our entire team is interacting with one another.  Investors, associates, and management team members meet, socialize, share ideas, and solve problems together.

Our March 2015 Agenda

Click here to download our full agenda for this last board meeting.

Here’s a quick summary:

  • Day 1
    • Speed Dating – We needed to help our investors get really deep on the opportunities for both expansion and improvement, and we wanted to expose them to a larger number of our team members, so we created a 3 hour Speed Dating experience.  We had 6 stations, each staffed by 2-3 associates who took them deep on a particular part of the product or the go-to-market strategy around the product.  They had 20 minutes to listen, learn, take notes, and ask questions, and 10 minutes to transition.  In 3 hours, each investor had rotated through all 6 stations in an intimate setting, with the opportunity to directly observe our company and our product for all that was good (and not so good!).
    • Executive Dinner – We made sure that there was time for the investors to build relationships with the management team, and even kept it super healthy (salads and light fare).
    • Texas Hold’em Tournament – That evening, we put away the work stuff and had an all hands poker tournament.  It was a ton of fun to watch a total of ~35-40 engineers and investors, marketers and management, sales and client success all squaring off in a fun game of Texas Hold ‘Em!
  • Day 2
    • Executive Breakfast – This was a second opportunity to deepen executive and board level relationships.  We made it optional, but everyone showed up.  While the dinner the night before was more social, this was a little more structured around strategic conversation and digesting information learned during the Speed Dating sessions.
    • Board Meeting (No Updates…  All Strategy) – This was the big test. We purposefully built no board deck, which felt a little awkward, but it was really freeing.  We had data on hand that we could pop on the screen to answer certain questions, but largely, this was 4 hours of fantastic strategic conversation.  The strength of our investors and advisors really shined through during this session.  We had well connected, deeply educated and experienced people working side by side with us to solve problems and exploit opportunities.  It was quite an experience
    • Investor Panel – After the board meeting and lunch, we held another all hands session, this time in the format of a town hall / panel style interaction.  The investors (now all clad in Windsor Circle Green Pants!) sat up front, with the entire company in the room.  We instructed our company that no question was taboo, and likewise instructed our investors to pull no punches.  Openness and Transparency is a key value for Windsor Circle, so these instructions were well heeded and we had a fantastic and honest conversation as a cohesive team about what the market looked like, what opportunities and threats Windsor Circle has, and what lay ahead for us as we continue our very rapid growth as a company.
    • People Helping People – Opportunity to Pitch to Our Investors – We sought commitment from our investors in advance to spend time with fellow entrepreneurs in our ecosystem here in Durham.  We basically created the opportunity and then got out of the way, so our peers could have direct access to our investors to pitch.  We understand that this was well received by both sides!

One of the Best Board Meetings!

All of our investors reported back that this was one of the best board interactions they’d had in a long time.  Here’s a quick quote from one of our investors.  (Sidenote:  I share this quote not to be pretentious, but rather of evidence that this calculated risk regarding the extended meeting format met with the results we’d hoped for).


Good meetings on Wed & Thurs.  You are the first CEO, in my experience, to successfully pull off a separation of ops and strategy.  Other CEO’s & boards have recognized the value of doing it but most of the time the strategy session devolves into ops anyway, or the strategy is pushed to the end of the meeting and some of the folks have already left.”

If you’d like to download the board agenda for more specific details, click here.

How Rockstar Leah Houde (Executive Director, Duke CE) Helps Execs Handle Difficult Conversations

Every quarter, Windsor Circle holds a “Team Day,” where we leave the office for a day and do three things:

  1. Volunteer in our community,
  2. Learn about “the science of teamwork,” and,
  3. Goof off a bit at Bull McCabes, our favorite watering hole.
Leah Houde, Executive Director, Duke Corporate Education

In this last science-of-the-team session, we enlisted the services of Duke Corporate Education, and specifically the talented Executive Director, Leah Houde.

Duke CE (located right here at the American Tobacco Complex in Durham, NC) typically coaches CEOs of F500 companies, and has been named by Financial Times as the best corporate education group in the world for 12 years running.  (Yeah, wow… mad props).


We wanted to arm our team with the tools necessary to have difficult conversations so that when the rigors of building a venture-backed business raised peoples’ hackles, that we’d know how to navigate hard conversations like bosses.  Here’s a quick summary of what we learned:

1. Mind the Gap!  (Inner Voices)

Imagine the following conversation:

CEO: “We’re going to triple the business this year!”

Employee (says out loud): “Right on!  Let’s do this thing!”

Employee (inner voice says): “Good lord…  how are going to do that?  And my quota is going to go way up.  This sucks and I’m scared!”

The gap here is palpable.  If the CEO isn’t actively listening and creating opportunities to get closer to the inner voice, she or he has a real problem.  The employee is rightfully showing enthusiasm and support.  The CEO is hearing agreement and buy-in.

But what’s really happening here is that the employee is feeling really scared about the change that is coming.

Here’s another example, from Leah’s presentation.

Source: Leah Houde, Duke CE
Source: Leah Houde, Duke CE


It’s important to do two things here:

  1. Mind the Gap – Just be aware.  We all have that little voice inside our heads keeping a running commentary of our lives, but if there’s a gap between what’s being said aloud and what’s being thought, you could have a serious disconnect.
  2. Create Room for Inner Voices to be Heard – In the short term, this could be providing for truly anonymous surveys or feedback mechanisms.  In the long term, it should be continuing to make deep deposits into the emotional bank accounts of employees and earning their trust over time.  The more genuine vulnerability and earnest attention to people’s opinions you can show, the more the gap can shrink, because people feel that they can trust you.

Remember, the bigger the gap, the bigger the problem.  Work hard to listen for that inner voice.


2. Intent vs. Impact

This is a big one.  Inside our own minds, we have years of context and conditioning.  We are masters of our own data and experiences.  So when we act, or make a statement, we do so with all of that context…  in other words, we intend to communicate a certain sentiment with the words we choose, based on what we know.

But this is problematic, because the person you are communicating with may not share your context.  They may not know what you know.  And so the impact of what you are saying may miss the mark.

Consider the following:

Prospective hire: “So, as a startup, how profitable are you?”

CEO (enthusiastically): “We’re not profitable at all, and have no plans to be!”

Prospective hire (inner voice): “I gotta get out of here… this is a sinking ship.”

In this exchange, the prospective hire is equating profitability with job security.  The CEO of the startup is excited about not being profitable, because in a high-growth, SaaS business model, if all of your other metrics are right (CAC, margin, churn, and growth rates) the last thing you want to do is slow down and try to get to profitability.  The explosive growth and lack of profitability, to the CEO, is a sign of rampant success!

In this scenario, the CEO would have been better served to ask “Great question…   Are you asking about the nuances of our SaaS operating metrics, or are you more concerned about our success and survivability as a firm?”  This would have aligned intent before the impact of a grandiose statement scared off this prospective hire.

Remember that your intent is tied to your own contexts.  Ask clarifying questions early and often when communicating so that the impact is what you wanted it to be.

3. Walk Me Down Your Ladder (of Inference)

Source: TedEd
Source: TedEd

Argyris (HBS) and Schon’s (MIT) Ladder of Inference is a construct for understanding how we as humans frame perceptions based on data that we have.

We observe data (bottom of ladder), apply reasoning based on our experiences and knowledge (middle of ladder), and then come to a conclusion (top of ladder).

We as humans evolved over millions of years to get to conclusions very quickly… and that’s healthy.  Those who couldn’t quickly surmise that fast things with large teeth were likely to eat them, were removed from the gene pool.  Those who could quickly arrive at this conclusion (“Danger!  Run!”) passed along this hard wiring to their progeny (us!).

So… relax.  It’s healthy that we quickly and automatically form conclusions.  We just need to be aware of them, especially when our conclusions are causing conflict.

Using the prior example, the CEO is working from a data set that is framed by years of executive experience in SaaS.  She has seen scores of examples of high growth SaaS businesses produce significant wealth by specifically not trying to achieve profitability, but instead by focusing on growth within the right SaaS metrics.  The prospective hire on the other hand, may have been a part of businesses that failed because they were poorly managed, did not have access to funding, and did not achieve profitability (self sufficiency)… and as a result felt real pain when they were laid off.

In other words, these two participants are talking about the same thing, but working from different data, processing that data in different ways, and ultimately reaching different conclusions that are in conflict with one another.

What’s useful about this paradigm is that it lends itself to a phrase that can be invoked when you are in conflict or disagreement with someone.  

“Hey, we’re seeing this differently.  Will you walk me down your ladder and help me understand your data points and your experiences so that I can understand the conclusion you are reaching?”

I started using this phrase, “walk me down your ladder,” almost immediately in our business and to good effect.  Yes, it’s a bit cheesy.  Yes, it feels a bit “corporate” to say “walk me down your ladder.”  But the benefit of clearly signaling that you care enough to try to understand the other person’s perspective, and that you’re willing to risk some cheesiness and business-speak to do so, is well worth it.

[Update: Since writing the initial draft of this post, I’ve had multiple Windsor Circle employees actually come tell me that they are using this technique all of the time, and not just at work.  One of them shared that he and his wife were in a heated argument, and he said, “this is gonna sound dumb, but walk me down your ladder.”  In a matter of minutes, they realized that they were arguing over nothing, and that by taking time to review their assumptions and underlying observations, they resolved the argument and got themselves back to a fun place instead of an angry place.]


We are targeting significant growth in 2015 at Windsor Circle.

We held a company wide meeting and specifically invoked these themes.  We acknowledged the inner voices of our team, who have largely not been in venture-backed, high-growth start ups before and who have not seen this sort of aggressive growth in their early careers.

We did this with phrases like:

 “It’s ok to be nervous about these big goals and these changes.”

“The big targets are going to mean a lot of hard work, a lot of risk, and indeed, some failure!   And that can be scary.”

“Those of you on variable compensation targets, primarily sales, are concerned because your quotas will go up.”

We then literally used the words (because everyone was trained on them), “let us walk you down our ladder so that you can see what the management team and the investors see, and then we welcome you to draw whatever conclusions you’d like from that data and reasoning.”  Certainly our hope was that our team would see what we see, but our goal was to align, not necessarily to convince.

Given the Windsor Circle core values of “openness and transparency,” and “facts, not claims,” we showed specific numbers to our entire team regarding the funding that we’re putting to work to make these growth goals a reality.  We showed how dramatically we’re ramping the product team, and the investment in the marketing team.  We showed comparison charts of how much more we’re investing in marketing spend and in which channels.

It doesn’t mean that people immediately snapped out of their own conclusions… that would be a silly expectation on our part as a management team.  But by earnestly listening to inner voices, thinking about our intent and impact, and using the framing of “the ladder of inference” we shifted the conversation away from the fear of the unknown, and over to a reasonable discourse of why all of the data suggests that this is the right time, and the right team, with the right resources, to get this done.

We just ended December at 151% of our best month to date, and Q414 at 142% of our best quarter to date.  We’re three weeks into January and we’ve already beat December.  We’ve got a lot of wood to chop in 2015, but I think we’re headin’ in the right direction!

Thank you, Leah and Duke CE, for being a part of our journey.  These are invaluable tools and we appreciate you helping us learn and leverage them.

Windsor Circle’s Compensation Philosophy

We spent some real time thinking about how we would approach compensation as a team now that we’re post-financing.  We wanted to maintain the discipline that got us to where we are, but also do a good job of executing on our values around taking care of our most important resource… our people.

Here’s where we landed (see below).  This now lives on our internal wiki so that all employees can get to it and so that we can all hold ourselves accountable to it.  In the same way that having clearly articulated our Windsor Circle Values (and trying to live by them), I think that this will help give us a “true north” when thinking about compensation.

Open to thoughts and comments…

Kicking the Doors Off the Hinges Every Day

Windsor Circle’s Compensation Philosophy

At Windsor Circle, we want people kicking the doors off the hinges to be here every day.  Part of making that a reality is giving people a fair financial compensation package and equity ownership in an exciting, high-growth company.

But money isn’t the only thing.  There are lots of places where you can make a lot of money and be miserable.  We don’t like miserable people, and don’t want them on our team.  We want hungry, ambitious, positive, fun, kooky people (and so far, that’s exactly who we’ve attracted into the Center of the Retention Automation Universe!).

We want people who love being here because it’s a meaningful place to be, with team members they really like, and extraordinary opportunities for personal growth.

So, our compensation philosophy will be guided by:

  • Fair compensation – We actively document data points externally and internally and purposefully aim for the 50th percentile of the market.

  • Equity ownership for everyone.  This is rare. We want everyone rewarded if we exit big.  This isn’t about making everyone a millionaire (that’s an incorrect expectation to set).  This is about sharing in the rewards if we get the job done and have a nice exit.

  • Loyal Citizens, Not Mercenaries – We want employees who are passionate about “us” and our mission (as “we” are hard to replicate!).  We don’t want individuals who are primarily or solely motivated by high compensation (as the highest bid is somewhat easy to replicate).  We seek loyal citizens, not mercenaries.

  • Find Diamonds in the Rough – We’re willing to take chances on smart, unproven talent.  In the first year, an inexperienced employee can expect to take a lower salary in exchange for being given significant mentoring, responsibility and experience.

  • Play to our stars – Our stars can expect higher compensation.  Not everyone can be a star, but the smartest, hardest working, most committed team members will earn special compensation for their contributions.

  • We care about the whole person.   We are intentional about our team’s health and wellness.  We work a little harder than the average bear at orienting ourselves towards taking care of our most valuable resource…  and in ways that completely “Shred the Box.”  Initially:

    • Wellness Consultant and Personalized Plans (pending)

    • Wellness Wednesdays

      • Massage (November 2014)

      • Chiropractic (pending)

      • Financial Planning (pending)

      • Flu shots, Checkups, General Health (pending)

      • Corporate Fitness Challenges and Goals (pending)

    • Telemedicine – Every employee has access to fast, convenient medical care via phone/internet. (November 2014)

    • YMCA Membership – use or lose it (8x/mo) (November 2014)

  • Optimization, not just Balance – To be clear…  we’re a venture-backed startup.  We’re not out for a nice stroll every Sunday… we want to win the Superbowl.  Expect to work ridiculously hard.  Expect to hit heights you didn’t think possible, and to be exhilarated and exhausted as we celebrate our victories.  Like an elite athlete, expect to be supported in ways that make you soar.

  • Building the Best Team Requires Letting Low Performers Go – Everyone’s outcome is dependent on performing well in every role, and if we can’t help an underperformer course correct, then we must have the courage to amicably part ways.  When we do so, we hold the respect and integrity of the individual in the highest regard.

  • Quarterly Bonuses That Reinforce Relationships – Every quarter, we name a bonus for the entire team when we hit certain revenue targets.  These aren’t financial rewards unto themselves.  They are things that draw us closer as people.  If we hit really big goals, then we additionally provide an opportunity for employees to engage their friends, family, and loved ones with a cool experience.

  • Insurance and Benefits – We will look to have a competitive health plan, with a focus on making employees healthy and well.  We will also emphasize value to the employee.  In this time of change in the healthcare environment, this means that we will leverage tax advantaged ways to deliver value, such as Health Savings Accounts.  We’re a smart bunch.  Doing a bit of thinking can add more value to our employees instead of taking a dumbed-down but more expensive standard plan. Retirement savings and other long term financial incentives will be considered as well.

Our Values Regarding Compensation

No Substitute for Ownership and Fair Compensation.

Foosball and free sodas are poor substitutes for fair financial compensation and ownership in an exciting, growth-oriented business.  Doesn’t mean that we won’t have fun.  And we’ll very likely have free soda.  But we won’t confuse the fact that our employees’ well-being, and that of their families, are of paramount importance to them.  The nice-to-haves are just that.  Nice to have.

Play to Your Stars.

Wow your top 10%. Excellence is hard to find. Once you’ve found it, secure it.

Risk * Execution^2 = Reward.

We’re building a world class software as a service company.  As a startup, we need people taking risks.  The more risk one takes, the more reward is embodied in the upside.  That said, we must execute against our plans to mitigate the risks, or the reward will never materialize.  So, risk times execution squared will be the lens we peer through as we think about financial compensation for members of our team.

How Rock Star CFO Tim Oakley Thinks About Hiring in the Finance Function

Tim Oakley, CFO of Appia and former CFO of iContact, is one of the Triangle’s best entrepreneurial executives.  With multiple exits and financings under his belt, and a commitment to servant leadership, we are fortunate to have him mentoring and guiding a generation of entrepreneurs (like me!) in the Triangle (the New Entrepreneurial Hub of the South).  Tim also formally does executive coaching at the Carolina Clinnic at UNC.

As Windsor Circle goes through the process of selecting and hiring a Director of Finance and Operations, Tim offered to spend some time with me thinking through strategy and candidates.

The first section is Tim’s “5 R’s of Finance.”  The following sections come from a scoring matrix that Tim shared with me.  I’ll use these subject areas to frame this post.  I’ll also offer suggested questions in italics to expound upon the areas in which one is qualifying a candidate.

The 5 Rs of Finance

This is a framework Tim shared with me for how to think at a high level about the G&A function.  I reframed it slightly to address how one hires in this function.

  1. Radar – Candidate has the systems, processes and management reporting that show issues early to be addressed and to capitalize on opportunities.
  2. Risk – Candidate can take calculated risks, identifying lower, expected and upside scenarios. The candidate should actively work towards “No Surprises” (especially on the downside!)
  3. Resources – Candidate needs to be able to allocate resources among multiple investment opportunities, and map them to present value of future cashflows (ie value), develop the people that work for her or him, and to support customers. Everything this function does should support “Selling Something to Somebody!”
  4. Reality – The candidate must collaborate with company leadership to define what the REAL story of the company is through monitoring metrics and relational and market information, and seasoning it with judgement and wisdom from her/his experience.
  5. Relationship – The candidate has to be able to built a trusted connection with the executive team and team members. This is especially true with the 15%-20% of the leadership team that is really driving the business (likely, but not always the CEO).

CFO Functional Knowledge – Day to Day

This section is from Tim’s scoring matrix, with elaboration based on our conversation.

Accounting, Financial Statements, and General Ledger (GL) 

This seems obvious but Tim pushed me here a bit.  There’s a difference between financial planning and modelling, and the act of closing the books on a routine basis.  Part of this is knowing how to handle accounting complexities in a subscription revenue business (such as deferred revenue schedules).  Another part of this is testing for the discipline to logically order a complex set of tactical requirements and keeping those trains moving on time.  

Tim shared that at iContact, he outsourced the bookkeeping function for quite a long time to a contract accountant.

Questions to ask during an interview:

  • Describe your experience closing the books and presenting financial statements to investors.
  • During the last audit, what did you find to be the most frustrating about the process?  What did you do to manage through it?
  • Imagine you’ve earned the job at Windsor Circle as Director of Finance and Operations.  Take 5 minutes to whiteboard your monthly, quarterly and annual responsibilities and then walk me through how you will manage it.

Payroll and Accounts Payable (AP)

Here, Tim was coaching me to think about the outflow of cash in one’s organization.  Getting everyone paid on time, and knowing how to manage vendors and contractors (and their payment terms) are critical skillsets, particularly during the early trajectory of a company given how crucial every dollar is.

Questions to ask during an interview:

  • Describe an instance where payroll was mishandled and what you did to overcome the error.
  • What is your philosophy on payment terms and how to pay vendors?
  • In the past, when faced with a cash shortfall, how did you manage AP to get the desired result?  What was the desired result?
  • What payroll systems do you have direct experience with?  If you earn the job here, what would you change about our current payroll system?

Accounts Receivable (AR)

Clearly, this is the inbound cash function.  In most businesses, these are payments from customers, but can also include payments from partners in the form of revenue sharing, commissions, etc.  As we scale from hundreds of clients to thousands of clients, with varying contract terms, and potentially across various products with different product and service profiles, this can get complex.  Tim wanted me to be sure I understood how someone in this function can keep a tight rein on the very source of life…  one’s inbound cash flow!

Questions to ask during an interview:

  • Describe the system you have used in the past to manage your client ledger.
  • How have you handled collections.
  • What critical measures do you use in this function? How will you know that you are collecting cash well?  (Days Sales Outstanding, or DSO, is key metric that should pop up in the answer).

Customer Resource Management (CRM) and IT Systems

I’m actually combining two sections here from Tim’s scoring matrix.  What (I think) I learned was that Tim was wanting to dig into a candidate’s ability to run the technology that runs the function.  CRM systems like or NetSuite allow one to keep all recorded interactions in a single place.  (At Windsor Circle, we strive to a corporate value of “Single Source of Truth” in our CRM and actively work to get everyone communicating through a single platform).

As he worked me through the IT systems component, he seemed very focused on the interface between the payment systems and billing technologies (at iContact, it was built into the customer facing app and required a pretty light implementation of QuickBooks to manage…  in other companies, the contracts and billing process are paper driven and may involve much higher degrees of complexity in the IT systems).

Questions to ask during an interview:

  • What CRM systems have you used in the past?
  • What complexities have you witnessed in the interactions between the CRM systems and the billing technology that you used in your prior roles?
  • Let’s say you won the position here, and had to completely revamp our CRM and billing systems…  whiteboard a plan for how you would tackle this and walk me through it.


An audit will be handled by an outside firm, so this line of questioning has more to do with how to manage an audit or review process.

  • Have you led an audit before?
  • What criteria is most important to you in selecting an audit firm?
  • What support systems and resources are required for a proficient audit?


Certified Public Accountant (CPA)

This is kind of a yes or no question.  Either the candidate has a CPA or not.  The knowledge you’re looking for here is an authoritative level of expertise with regards to Generally Accepted Accounting Practice (GAAP).  This, too, is a skillset that can be contracted in, but having someone inside your firm with a CPA provides for a level of efficiency, not just in audits, but in the general running of the finance function.

Planning and Analysis

A key indicator of expertise in this area is deep financial modeling capabilities.  In our selection process, we put one of our candidates under NDA and had her/him dig deep into our existing model with recommendations and analysis.  If the prior functional areas have to do with the tactical aspects of running the business, this subject area has to do with the strategy of running a business. One must quickly be able to model various scenarios, answer what-if statements, and think about future metrics assuming various aspects of the model come into being (or don’t!).

Questions to ask during an interview:

  • I’m going to have you sign an NDA, and then provide you with our financial model.  I’d like you to hit hard and pull no punches in preparing the 5 top things you’d modify about our business and our financial model.
  • In your opinion, what are the hardest parts of the financial model to get right?
  • Whiteboard the major aspects of your financial model and talk me through interdependencies.

Mergers and Acquisitions (M&A), Fundraising & Capital Markets

Deep expertise here is usually a CFO-level function.  Managing the complexities of due diligence and deal terms, as well as bringing the implied trust and connections of one’s personal network, are core aspects of this functional area.  If you’re hiring for a manager or director, exposure to these skillsets would be a plus, but perhaps not a requirement.  If you’re hiring for a CFO, they are a must.

Questions to ask during an interview:

  • Have you been through an acquisition?  Please describe the scenario and your role in it.
  • Describe your experience with fundraising?
  • What are the merits of venture debt versus equity?  Educate me on the terms that I’m likely to encounter in the market?
  • Have you ever been on a team that did an IPO?  What was that like?  What did you do well?  What did you do poorly and how did you overcome that?

Business Acumen

When Tim hit this area, it became clear to me that he was borrowing from a fair amount of intuition from years of experience.  What he seemed to be looking for was a candidate’s ability to rise above the noise of the function and sense what was happening in the business and to be an active participant in the prediction of what would happen next.  This also has to do with savviness…  sensing what’s happening in the team, in the market, and in the ecosystem.  I perceived here too that deep business acumen was either an indication of a rising star or someone that had been around the block a few times.

Questions to ask during an interview:

  • Describe where you see SaaS, as a concept or an industry, evolving to in the next 10 years.
  • Describe a hunch or a prediction in your current role that came true.  
    • How did you communicate that hunch?
    • When it came true, describe the reaction of your peers?
    • What would you have done differently?
  • You’ve gotten to know our business.  Make 3 predictions and back them up.

Fitting the Candidate

There were several other important criteria that Tim looked for in his matrix:

  • Rapid Growth Company – There’s no doubt about it…  the fast pace and ability to make decisions in the absence of data points is a critical ability.
  • Executive Team/Board/Culture/Communications – One could describe this as a test of anyone coming into the organization, but given that this person has to interact with a range of stakeholders on a variety of important topics from hitting revenue targets, to “zero cash day” to payroll, it’s important that you select someone that will fit well.
  • Tech Industry Experience – For us, one of the key aspects of this vector is Software as a Service subscription revenue concepts.
  • Wants The Position/Hungry/Something to Prove – Again, these are good things irrespective of the role.  In the finance function, I’ve now seen a couple of scenarios where a FP&A (financial planning and analysis) person from a large firm was actively seeking are more generalized role in a startup.  The hunger for the exchange of risk for higher responsibility, greater title and a more diverse set of learning experiences is critical.
  • Size of Company – Related to high growth, but different in that a small company requires everyone to wear lots of hats, and usually in a very unstructured environment.  In small companies, everyone has to be willing to get dirty and get the work done.  Candidates from large organizations may say they value this freedom and flexibility, but if their resume reflects only large company experiences, dig deeper here.
  • Managed and Led People Human Resources – Tim really pushed me here.  One of the candidates that we considered hadn’t managed others before.  This function has to manage both internal and external stakeholders to do well.  He asked me several times about my confidence that our lead candidate could step into this capability effectively, or if we’d run into issues with inexperience on this front.


Kicking Off with New Investors – Building Team at Every Level

We closed and announced our $5.25MM Series B in the last few weeks.  It was crucial to me that our shareholders, employees and vendors (which together comprise the Windsor Circle team!) have the opportunity to really engage and build relationships.  So, we created a very intentional and open set of events at the first board meeting with the new investors to really bring the humans involved in this shared journey to the forefront and to really weave the fabric of the team, writ large.

Stakeholders from all aspects of the team commented on how fruitful (and unique) this endeavor was, so I thought I’d share it.  Can’t claim it as a best practice given the sample size of having done it one time, but it “felt” right.  

(In the interest of time, I’m just cutting and pasting the original proposal with some edits)….

———- Forwarded message ———-
From: Matt Williamson
Subject: Windsor Circle Board Meeting Proposal – July 30 Social, July 31 Meeting
To: <*********>

Team – 
As you know, a smooth functioning board is as important to me as a smooth functioning internal team.  So, let’s have some fun and do some good business, too, during this first board meeting, and let’s have a mix of full team and board specific functions.
We won’t go to this depth every time…  but I’d really like to dig deep and get the relationship set nicely on this first one.
So…  here’s what I propose:
Wednesday, July 30 – Social (Full Team)
6:30pm – Happy Hour at WC HQ
8:00pm – Walking Tour of Explosive Growth in the Bull City (Board, Mgmt, Vendors) – I’m working to get Matthew Coppedge, COO of Downtown Durham, Inc. to guide this tour… he can speak to interesting aspects of both the history of Durham and the amazing growth that’s happening right now.
9:30pm – Ice cream social at the Parlour
Thursday, July 31 – Business
7:00am – (Optional) 5k Downtown Durham Run at Marriott Downtown (Anyone)
9:00am – Investor Panel and Bagel Breakfast at WC HQ (Full Team)
10:00am – Board Meeting at WC HQ (Board + Mgmt team)
12:30pm – End
Let me know what you think.
p.s. – Quick side note:  As you know, one of our strongest corporate principles is openness and transparency.  During the panel, you may get really open questions about the process of fundraising, the rigors of high growth, what you’re seeing in the marketplace, etc.  It’s ok to answer very openly.  We talk about things as sensitive as how many paychecks we have left, etc, and it builds really high levels of camaraderie and trust in our team.  We’re honest with ourselves about where we fall down and where we need improvement (in add’n to a lot of celebrating about the great things we’re accomplishing).  Net: we trust each other b/c we work hard on it.  As part of the team, you have full license (and my expectation!) to share your thoughts/perspectives openly.

“Silicon Acres?” Branding the Entrepreneurial Hub of the South

During the Google Demo Days competition, Jimmy Goodmon of CBC New Media shared the story of how his father, Jim Goodmon, had a vision of uniting the several communities of the Triangle (Raleigh, Durham, Chapel Hill) with a centrally located, massive professional sports complex that would capture the two franchise expansions in the NFL and NBA at the time.  Goodmon’s argument was that the combined viewership of the MSA represented by these cities was equivalent to that of Charlotte…  but that we had to pull together.  Ultimately, the three towns and their respective governments couldn’t quite get together the votes to pass this vision, and the idea subsided.

I’m as passionate about Durham as you’re going to find… to the point where my wife and friends sometimes call me “Captain Durham.”  Man, I love the Bull City.  But when I originally wrote this email to then-Governor Bev Purdue about the Entrepreneurial Hub of the South, I bent my vision towards a larger footprint.

I’d like to take another step in that direction.  Branding has such a powerful effect on the formation of ideas and the unification of effort among individuals and groups.  The Research Triangle Park was a brilliant strategic deployment of public-private endeavor in the back half of the last century.  It is thought of, however, as that work place in the middle of the three counties.  Still great.  Still visionary.  But it represents a bit of a fourth locale, not an amalgamation of the three locales that contribute to it.

There is robust entrepreneurial energy, programs, incubators and efforts happening throughout the triangle and enmeshed in the four major universities (UNC, Duke, State and Central).  Another Goodmon (Michael), and his chief strategist Adam Klein, are exploding onto the national scene with the American Underground and AU@Main brands (which has attracted the attention of Google, who has officially named it as a Google Tech Campus).  Innovators like Christopher Gergen are spawning concepts like HQ Raleigh, Bull City Forward and Think House.  Incubators like the Start Up Factory (located in the American Underground) are churning out promising new companies under the empowering guidance of veterans like Dave Neal and Chris Heivly. The energy is off the charts and the sheer power of the job creation and innovation is humming.  You can literally feel it.

I think it’s time we unite our communities in the way that Goodmon originally envisioned with sports, and with the power that the Research Triangle Park brought to NC to attract high paying technology jobs.

As we continue to frame the Entrepreneurial Hub of the South, let’s brand this in a way that is telling of what we do, reflective of our roots, and unifying in the way that allows for each community to thrive in place, but that unites us all.

As the first brainstorming of the brand, I propose “Silicon Acres” playing off the Silicon Valley metonym.  It provides reference to our agricultural roots (of which I am proud).  It also avoids the trappings of locking into a single brand (Bull City, Oak City, etc.).  All of us can be fiercely proud of our own cities, while unifying around a brand that gives us a sum that is greater than its parts.

I’ll toss out a few more:

  • Silicon Triangle
  • Tech Triangle
  • Tri-tech Area

For a bit more depth, here are links to the naming of Silicon Valley and to other locales playing off of this metonym.


The Entrepreneurial Hub of the South

I wrote this email to then-Governor Bev Purdue back in Oct of 2012 after attending an entrepreneur-focused luncheon at the Governor’s mansion. It didn’t go anywhere at the time, but aspects of this vision are being implemented, so I thought I’d post the vision publicly and contribute to the noisy, rambunctious start up process that I love!

———- Forwarded message ———-
From: Matt Williamson
Date: Mon, Oct 8, 2012 at 11:22 AM
Subject: NC – The New Entrepreneurial Hub of the South | Re: N.C. Innovators Entrepreneurs Luncheon
To: “Perdue, Bev” ,

Governor Perdue and Don –

Thank you for hosting. It was an honor to attend.

I’d like to share an idea that maps to much of the conversation. I’ve been thinking about it for two years, but haven’t acted on it as I’ve got this little thing (building Windsor Circle as a start up software company in downtown Durham!) that has been keeping me occupied.

I’ll share the vision here:

NC – The Entrepreneurial Hub of the South

The vision is akin to the concept of the Research Triangle Park in that it creates real reasons to attract talent and resources to NC. It’s a bold vision, much larger than springing up a co-working space or a campus. We need more than that. Every state in the union is embarking on similar incubator programs.

What we need to do is create an environment where the best and brightest innovation talent in the country and the world is relocating to North Carolina to start companies because it is advantageous for them to do so. The following 5 point plan would create that environment for attracting talent:

  1. Leverage Strengths – Strong Universities, Good Business Climate, Great Family Environment for Workers The first part of the vision is to commit everyone to get on message. We have an exceptionally strong academic climate in NC at the collegiate level (we need to work on the school system that feeds it, but that’s a different conversation). The UNC system, plus powerful research universities like Duke and Wake Forest make NC a great place to build ideas and find talent. The business climate is friendly and the costs are low… as said in the luncheon, NC can offer a very cost-efficient climate in which to build businesses. And finally, from a human perspective, this is a great place to raise a family, with beautiful natural resources all around us, and very affordable real-estate. These reasons should be trumpeted to entrepreneurs far and wide as reasons to locate here to build their businesses and their lives.
  2. Build Incentives – Free Work Space, Free Living Space for 2 Years, plus Lifestyle Incentives – As North Carolina continues to shift from agriculture and manufacturing to technology and healthcare, there is an abundance of buildings and warehouses, located in and near downtown areas, often in close proximity to universities of great importance, at rock bottom prices. A concentrated program to stimulate development of these buildings into work and living space would create more than entrepreneurial incubators… these would be havens… communities… tight concentrations of like-minded individuals who want to take risks and create value. Top entrepreneurs worldwide would be offered 2 years of free work and living space if they relocate here (see below). Clearly, you’d start with Durham, Raleigh and Chapel Hill, but once proven, more can be built around the state. Additionally, programs already exist to make it easy for military personel to get lifestyle incentives (insurance, group buying and discounts, discounted entertainment, etc). We could plug directly into this network. (Note the additional benefit of elevating the brave men and women who are risking it all to start business and create employment to the status of those who brave it all to defend our country… this analogy creates massive emotional incentive to take those risks. “She serves our state by being an entrepreneur!” would have the same ring as “He serves by risking it all in the military to defend our country!”
  3. Market “NC Entrepreneurial Hub of the South” to Top Talent Worldwide – Here’s where this becomes more than just a bunch of in-state incubators (which every other state is doing right now, too). We take all of the reasons listed above and hit the road. We get the top entrepreneurs in our state (like Goodnight and Szulik) and hit the road. We pitch the program to the best IT and healthcare students in the top 20 universities in the country and the top 10 in each of China, India and Europe. The goal of this roadshow is to recruit the top talent and ideas to NC. Imagine snagging the best talent that is graduating from Stanford, Harvard, MIT…. from the top universities in Bangalore, in Shenzhen, and other international technology hotspots. The best NC talent (both business and academic) would be identified to chase the best opportunities. If you find a promising healthcare start up in India, perhaps Quintiles CEO would be called in to help recruit the company to NC.
  4. Connect VCs to NC – There are two parts to this. My mentor Ed Paradise at Cisco could help us get telepresence in each entrepreneurial community. All companies would be able to set up powerful virtual board meetings to help shorten the distances that sometimes get in the way of investments here. Secondly, we build and brand direct flights in NC from the major investment hubs as the “VC Jet Set.” We already have direct flights to most of these, but branding and elevating them as a “set” makes it obvious that we’re serious about getting capital here. It’d be a simple exercise to add smaller fractional jet coverage as well. Imagine the power of putting an “entrepreneur only” get with 12 seats together on a monthly basis and putting the most promising companies who are raising money on a NC-funded road show. Consider it a VC highway to NC… worthy of the investment than any other infrastructure would require.
  5. Build “Entrepreneurial Free Trade Zones” – You already have a model for how to create economic incentives with the FTZs that exist in NC. You’d basically create EFTZs to support this program. You’d add the qualification of size, or growth, or investment, or something to make sure you were truly rewarding entrepreneurial companies that had the possibility of high growth and the creation of jobs and wealth.

“NC Entrepreneurial Hub of the South” is a big vision. Over 20 years, we’ll end up developing 30 buildings into Innovators Communities and EFTZs. We’d be on a worldwide stage, driving hard to recruit the very best talent and ideas to our state. We’d be creatively putting NC talent (both incumbent and recruited to NC) in front of the best VCs in the world.

We’d be taking a gamble not unlike that which a group of committed individuals did when they put together a plan for the Research Triangle Park to great effect many years ago.

We’d be displaying the same courageous, innovative risk-and-reward mentality that Entrepreneurs have to summon on a daily basis.

And… if we’re right… North Carolina will be heralded in the same breath as San Francisco, Boston and NYC. Our first goal would be to land in this top ten list. And then work our way to being one of the top 5.

I’m excited about this vision and happy to discuss in more detail.

With warmest regards,


Matt Williamson
Windsor Circle

O: 919.822.2014 | M: 919.724.0931 |
Calendar (Eastern Time) | LinkedIn | @windsorcircle

4 Min Demo | Hot on VC Shopping List | Top Company to Watch in 2012

Thoughts on the National Circles program, and our involvement in it.

The following email was a bit of free form thought processing that stemmed from a dinner conversation with friends about Windsor Circle’s pending commitment to participate in the National Circles program (being implemented locally by REAL Durham, of which Mel Williams is an active contributor).

It involves us making an 18 month, bi-weekly commitment to a single family.  It’s a big commitment.  Thoughts below….

———- Forwarded message ———-
From: Matt Williamson <>
Date: Thu, Jul 24, 2014 at 7:53 AM
Subject: National Circles program
To: ——

Friends –


This is the program that REAL Durham program we were discussing last night.

It’s based on the National Circles Program.
Last night’s conversation was helpful in processing the risk we’re taking as a for-profit entity considering a deep commitment to a family.  As I was reflecting, I thought I’d capture reactions, both positive and negative, as we’ve talked about this internally and externally.
  • Positive Reactions
    • It’s nice to see a company making a deeper commitment
    • It’s a good reflection of who the people in WC are as individuals, and who the company is as a group of individuals
    • This type of commitment is what makes Durham’s brand of entrepreneurship unique.
  • Negative Reactions
    • You might not get out of it what you think you will.
    • Companies may not be set up to deliver these sorts of services, and this could lead to some degree of failure for both the family and the company.
    • This was top down / mandated.  Is WC doing this b/c Matt wanted it done?
    • There’s only 4 people involved in the core group.  What about everyone else?
    • The great white knight…  you think you can ride in and be smart and make change without really knowing the people or the environment.  Lots of examples of this failing at a massive scale.
As I’ve contemplated this effort over the last few weeks, I’ve wrestled with:
  • Why are we doing this?  What attracted me / us to this (versus more standard corporate volunteerism, or volunteerism at all)
  • What are the risks of a for-profit entity doing this versus a non-profit?
  • What’s my role?
  • What do I hope to get out of this?
  • What value am I giving to the family, to the team, to the community, to my company?
I’ve observed, broadly, the following perceptions of businesses and business-types at or near the intersection of poverty issues and trying to address them.  These observations are informed not just in this effort, but also at the helm of various Habitat efforts over the past 20 years:
  • Companies don’t do enough
  • Greedy
  • Too focused on numbers, not focused enough on people
  • Companies / business people aren’t to be trusted
  • When engaged in community effort, company’s have ulterior motives (mostly around taking credit for doing good in a community, even if the good isn’t that impactful, and especially if that token effort is being used to distract from negative community impact driven by the company’s business practices).
I don’t have the answers to much of this.  They’re just observations, and probably skewed as I am one person, with one set of experiences, and I don’t always get it right (I usually don’t get it right).
So, maybe to attempt to answer one of my own questions….  Why are we doing this?  What attracted me to this?
I’m attracted to the National Circles program for two reasons.  
First, the model is showing quantifiable success in alleviating the conditions of poverty.  It’s early.  We’ll see if these numbers hold, but I can’t deny that I’m interested in programs that can show real progress.  And I care about my community, and the people in it, so I was attracted to the effort because it could make a difference in my community.
Second, I’m intrigued by the level of commitment and connection being implied here, and that no company to our knowledge has attempted this.  There’s nothing wrong with the team volunteering once a quarter (and we do).  But this is about getting involved with a family in our community…  in my community… every other week for 18 months.  Not painting walls…  Not picking up trash…  (we do that already and are happy to do it more)….  But opening ourselves to what may be some painful introspection about the disparities in our community.  Being vulnerable during the training to be told just sit there and listen…  that your family leader is going to be smarter/better/more capable than you are at directing what will make change in their lives and in their communities.  To risk becoming emotionally connected to others who live very different lives, and wrestling with what that may entail in our own lives.  To deal with the unpleasantness of being perceived as a person of privilege that is doing this for the wrong reasons (this one is particularly hard for me to digest).  And, maybe, if we risk that much commitment, a family in our community may make real progress in their own journey.  And, as this unfolds, we as allies to this family might make real progress in our journeys as well.
I don’t know where this will go.
I’ve been a bit surprised by some of the negative reactions to attempting this.  On the face of it, one would think that a group of people, organized for whatever reason, who wanted to help implement a program that is showing real success in other locales would be a good thing.  There’s something about the fact that our group of people happens to be organized as a company (versus a civic organization or a church group) that seems to make people uncomfortable.  Maybe it’s in the way that I’m presenting it.  Maybe there’s an inherent distrust of corporations (and perhaps well earned).  Maybe corporations can be good at creating opportunities for its individuals to do good work, but that they are inherently poorly suited to engaging in that work directly.  I don’t know.
All this said…  entrepreneurs take risks.  I think we’re going to give it a go.  It’ll be an interesting journey, with an uncertain outcome.  But I’m excited to be trying, and I’m pleased that the people in my company are the types that would even consider it.

The Weekly Planning Sheet

Years ago, I spent some real time digging into Stephen Covey’s 7 Habits of Highly Effective People.

In quick summary, his thesis is:

  • He studied a bunch of very successful people (not just financially, but those w/ high degrees of respect in their community and having accomplished interesting things but not at the sacrifice of their families and friends).
  • He tried to isolate what was similar in how these people lived their lives (hence the 7 habits, see below, copied from wiki).
  • In essence, these people think of their legacy, plan long term objectives that are in line w/ the legacy they want to leave, and then proactively take action against them.  He suggests a weekly planning framework to operationalize this thesis.

It’s been very effective for me personally.  I’m not a “Covey-head,” and won’t project that it works for everyone in all cases.  But I do know that most of the interesting accomplishments in my life have been because I was thinking about the person I wanted to be remembered as when it’s all said and done, what creative and fun life experiences I wanted to have to get me to that place, and then having a plan for taking action to drive me towards those goals.

My Most Recent Tracking Spreadsheet

Over my career, I’ve swayed back and forth between good usage of the methodology and not using it.  In this most recent return to the methodology, I built it Google Spreadsheets and discipline myself to spend time each week.  I’m not perfect at it, but it helps to keep things balanced when I do.

Here’s my sheet: 7 Habits Tracking Template


In case you’re curious….

7 Habits of Highly Effective People (taken from Wiki)

  • Habit 1: Be Proactive Take initiative in life by realizing that your decisions (and how they align with life’s principles) are the primary determining factor for effectiveness in your life. Take responsibility for your choices and the consequences that follow.
  • Habit 2: Begin with the End in Mind Self-discover and clarify your deeply important character values and life goals. Envision the ideal characteristics for each of your various roles and relationships in life.
  • Habit 3: Put First Things First A manager must manage his own person. Personally. And managers should implement activities that aim to reach the second habit. Covey says that rule two is the mental creation; rule three is the physical creation. Interdependence
  • Habit 4: Think Win-Win Genuinely strive for mutually beneficial solutions or agreements in your relationships. Value and respect people by understanding a “win” for all is ultimately a better long-term resolution than if only one person in the situation had got his way.
  • Habit 5: Seek First to Understand, Then to be Understood Use empathic listening to be genuinely influenced by a person, which compels them to reciprocate the listening and take an open mind to being influenced by you. This creates an atmosphere of caring, and positive problem solving.
  • Habit 6: Synergize Combine the strengths of people through positive teamwork, so as to achieve goals no one person could have done alone.
  • Habit 7: Sharpen the Saw Balance and renew your resources, energy, and health to create a sustainable, long-term, effective lifestyle. It primarily emphasizes exercise for physical renewal, prayer (meditation, yoga, etc.) and good reading for mental renewal. It also mentions service to society for spiritual renewal.


Should you work at a Start Up? (Cross post from Bessemer)

Note: This article, originally in Venturebeat and cross-posted on the Bessemer Venture Partner’s website was so spot on that I’m quoting it in it’s entirety.  

Source: Bessemer Venture Partners Blog



Should you work at a “start-up”?

January 2014

This article was originally published by Venturebeat

I recently made the switch from start-up to VC, joining BVP after three years as part of the team at Foursquare. Recently, people have been asking me a lot about my experience switching careers and what they should consider when thinking about transitioning into the start-up world. Over the course of these conversations, I’ve boiled it down to four questions that I think are worth asking yourself before taking that leap…

1) What is your definition of “start-up”? – The phrase “start-up” can be misleading, describing businesses in many different stages. Be honest with yourself about the level of risk you’re willing to take – do you want to join a company with traction, financial runway, and one that will give you the opportunity to learn from experienced people, or do you want to join an earlier stage company with more potential upside, but more uncertainty? Your experience will largely be based on the company’s size, financing history, and experience level of the people you will be working for and with. With just 20 colleagues and less than $2M in funding, Foursquare was a different company when I joined than the company that I left three years later with 170 employees and over $100M raised, but it was definitely a “start-up” throughout

2) Why do you want to work there? – If you’re thinking of joining a start-up because it sounds cool or your roommate is doing it – don’t. Make sure you think the company has great leadership and a product or service you can get behind. Sure, the offices will likely be a fun place to spend your days compared to your current corporate digs (and there might even be beer on tap), but things aren’t always easy when dealing with the ups and downs of an organization finding its way. Make sure you are excited to be in that space going forward, as you will likely be gaining expertise that will guide what you do next.

3) Are you ready to define your role? –  The earlier in the company’s life, the more you will have to dictate how you spend your time. Earlier stage start-ups have an endless number of things they could be doing. No matter what your role is, it will be largely up to you to prioritize your time and figure out how to add value. Nobody will be holding your hand or giving you constant feedback, so understand that is what you are signing up for.

4) Have you cut through the hype? – If you want to know how well a company is really doing, what it’s like to work there, and whether or not it’s a good fit for you, then you need to talk to current and former employees. One thing you learn quickly while working at a start-up is that there is often a massive disconnect between perception and reality. So get connected or introduced to people who know the real story.

At Foursquare, I was lucky enough to work with smart, passionate colleagues, experience rapid growth and the associated growing pains first hand, and witness fundamental product and strategic shifts. It was an amazing team to be a part of and the operating experience has served me well in my early days of working with entrepreneurs. If you can get comfortable with the answers to these questions, then go for it.

Foursquare team meeting, June 2010 (photo by Mari Sheibley)

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