Startup Founder Thoughts —Scaling a Personal Board of Directors

Over the past 4 years, I’ve been honing a philosophy rooted in the concept of a ‘Personal Board of Directors’. Not only have I applied this to myself as Co-Founder/CEO of WayScript, but I am contemplating pushing this as a company building mandate for all managers within the organization.

A Personal Board of Directors (PBoD) is the concept of intentionally surrounding oneself with a team of mentors, advisors, and friends who are invested in your professional successes and have relevant subject matter expertises.

Like a corporate board of directors, I meet with each member of my PBoD on a regular cadence to give updates, get feedback, and ask for advice. A PBoD requires acknowledging your weaknesses and making sure you have Directors who cover those areas.

Applying the Personal Board of Directors to my experience as CEO/Co-Founder of a startup.

Since 2018, I’ve been running a venture funded startup called WayScript. For the first 1–2 years, I spent most of my time on product and writing production code. As we’ve grown (~20 employees), my job has fundamentally shifted. Today (along with my Co-Founder Lane), I am focused on defining our vision & roadmap, company building, monetization, customer success, recruiting the highest quality people, building a healthy company culture, and communicating with investors.

From early on in my entrepreneurial journey, I set out to build a PBoD. I have found the benefits to be immense for my personal decision making. Having a PBoD, like having a great mentor, let’s me tap into the wisdom of those with more experience so that on average I make fewer mistakes.

Key Criteria for adding someone to my Personal Board of Directors:

1. Do they cover a weakness I have?
2. Do they have relevant subject matter experience?
3. Are they able to commit enough time? (Usually between 4–10 hours / month)
4. Do we work well together?

If the answer to these questions were yes, then I was prepared to offer them advisor equity in WayScript to join my PBoD.

One PBoD case study example — Tom Berger

Tom Berger was introduced to me by a mutual contact in our network. Tom is a veteran marketer (currently at Bolt) who has immense experience in developer products (My startup WayScript is an Internal Developer Platform).

Here is an example of how I applied the PBoD Key Criteria to Tom:

1. Do they cover a weakness I have?

Yes. When starting WayScript, Lane (my Co-Founder) and I both lacked experience in digital marketing roles (or any marketing for that matter). Therefore, I quickly recognized that marketing was one of my weaknesses but was fundamentally crucial for my role. Therefore, I need strong marketing representation on my PBoD.

2. Do they have relevant experience?

Yes. Tom was a VP of Marketing at DigitalOcean and has had a long career focused on developer marketing.

3. Are they able to commit enough time?

Yes. Tom and I spoke about this and agreed on a workable time commitment on both sides.

4. Do we work well together?

Yes. Initially, Tom and I decided to have a few ‘practice’ sessions to make sure that we were both gaining from the advisorship. It became obvious very quickly that this was a great match.

Because the PBoD key criteria was met, we offered Tom formal equity in WayScript to become an advisor. Tom has been on my Personal Board of Directors ever since.

Side note, early on for advisors we used the common FAST agreement.

My Personal Board of Directors

Here are some of the other roles I have brought onto my Personal Board of Directors. Most of these individuals I meet with weekly, some monthly, and others quarterly. Really it is up to you to determining how you want to run your board.

• CEO Coach — An advisor with immense company building and startup experience. She helps me think through macro to micro challenges that come with scaling a startup.
• Fundraising Advisor — An advisor with deep knowledge of fundraising to help us assess terms, offers, running a fundraising process, etc. For this person, we generally speak once or twice a quarter.
• Sales Advisor — An advisor who has experience building a sales organization (SaaS inside sales). I meet with this person bi-weekly.
• Product Marketing Advisor — An advisor who helps us think through product and positioning based on customer feedback and market trends. I meet with this person monthly.
• Business Partner — Ok, maybe this one is ‘cheating’. But I consider my Co-Founder Lane to be an important part of my PBoD. I meet with Lane daily.

The impact of my Personal Board of Directors has been immense. In startups, there is daily ambiguity and new challenges. Having a team around me that keeps me ‘from guessing’ and enables me to tap into their experience has been a fundamental force in the success we’re having.

Scaling an organization with the PBoD philosophy.

I’m envisioning the impact of a company built on the PBoD framework. Mainly, building an organization where

Every manager and team leader in the organization is encouraged and empowered to build their own Personal Board of Directors.

The business should plan for and enable equity allocations to these PBoD members.

So how might this work in practice and what might the benefits looks like?

How this might work

Any employee in a management role is automatically PBoD eligible. Within the organization, a culture expectation must be built around the benefits and expectations of PBoDs. Perhaps a part of an employees annual review includes a portion on their current PBoD status and outcomes.

When a manager wants to add an advisor to their PBoD, they would undergo the following process:

1. An application — In this application, the manager must identify the key criteria for this advisor. Mainly, a strategic fit (to be approved by their manager) plus an agreed upon working cadence. If approved, a predetermined level of shares are granted (standard advisor vesting) to the advisor.
2. Documentation — Manager’s are expected to document their PBoD calls and progress. Because PBoD advisors are given shares/equity, it is important to confirm that they are continuing to contribute to the development and decision making of the manager.
3. Expectations — The key goal of PBoD’s for managers is support for their weaknesses and decision making. Therefore, managers should also make an effort to help newer managers with how to construct PBoD’s including helpful roles, etc. The key idea is company-wide buy-in around the benefits of this model for better, wiser decision making.

Conclusion and Room for Thought

A Personal Board of Directors has been one of the most impactful things I’ve done to improve as a CEO. My guess is that a lot of company leaders have something similar to a PBoD already. However, I think there is real value in codifying and running a PBoD with as much seriousness as running a corporate board of directors meeting.

As far as I know, an organizational PBoD strategy has never been systematically applied to a company’s leadership/manager by it’s executives. Therefore, I lack data about how this outcome might improve performance over time at an organization.

To try this, my instinct is to push this philosophy onto the WayScript managers who report directly to Lane and me. If we find it successful, we would then have those managers promote the philosophy down to managers working for them (when that is the case for our company size).

One last thought, I haven’t tried the idea of PBoD board meetings, where the full board of directors gets together for a presentation/update once a quarter. I will think more on how this might work and if there would be any added benefits to my PBoD all knowing each other and working together with me.

About Me

Jesse Orshan — I am the CEO/Co-Founder at WayScript. I have an MBA from Harvard Business School and B.S. from Cornell University.

WayScript is an internal developer platform (IDP) that makes it easy for Business Technologists to write and deploy secure code for their team’s internal tools, data pipelines, and analytics. With WayScript, technologists do not have to rely on core engineering/SRE teams to build and deploy automations, scheduled tasks, and other business processes. WayScript is SOC-2 Type 2 compliant, highlighted as a key technology partner by New Relic, and trusted by teams at Volvo, Heap Analytics, Hopper, Shopee and more.