Business & Legal
Bluemercury, Board-Ready Bootcamp, Chris Comparato, Foley Hoag, Jim Heppelmann, Live, Marla Beck, PTC, Samita T. Ali-Khan, Toast, Yogesh Gupta. Progress, Zingeroo, Zoe Barry

What Do CEOs Want from a Board? Insights from Board-Ready Bootcamp

MassTLC’s Board-Ready Bootcamp is designed to improve the quality of board governance and composition at tech companies by providing a high-impact curriculum on board fundamentals, strategy, and governance. The Fall 2022 cohort kicked off with an exciting CEO Panel featuring a topical discussion on the topic of “What do CEOs want from a board?” Speakers included moderator Samita T. Ali-Khan of Foley Hoag and panelists Chris Comparato of Toast, Zoe Barry of Zingeroo, Yogesh Gupta of Progress, Jim Heppelmann of PTC, and Marla Beck of Bluemercury.

Here are some key takeaways from what they had to say. 

On the function of a board

“I think about the purpose of a board in 4 dimensions- 1st: Expertise and guidance, look to the board to fill in and be an extension of the leadership team while weighing in to add value. 2nd: The ability to problem solve and pass judgment, supports the decision-making responsibility that the board has. 3rd: Governance is all about guidance and making sure the company has the guardrails. 4th: Be a good coach to the CEO, it can be the loneliest job on the planet, and you need that board to be both a coach and a sounding board.” – Chris Comparato, Chairman & CEO, Toast

“Public boards are obligated by law to protect the interests of the shareholders. Ask, does this company have a good strategy and a winning strategy? Are they following the regulations? Regulatory compliance is why public companies have boards and make sure everything is done by the book so to speak. In a private board, a lot of the key investors are in the boardroom but in public companies you have proxies.” – Jim Heppelmann, CEO, PTC

“As a public company board member, you are overseeing strategy, as a private company board member the job is, ‘What do the CEO and the Senior Management team need?’ The private board’s function is much more focused on being there when they need you while the public board’s function is regulatory oversight. Regardless of public or private, boards are always responsible for the financial oversight-they need to understand the financials backward and forwards.” – Marla Beck, Founder, Bluemercury

“Character and commitment. When times are good everyone is great but when times are tough commitment and character shine through. This can be extremely difficult to find, make sure you can make the commitment and that you have time.” – Yogesh Gupta, President and CEO, Progress Software

“From a CEO’s perspective, determining whether I think that person is qualified to hire and fire me. Do they have the expertise to help this company not get sued? Also, regarding deal-making, can you help me make a deal? As a chairman, that is essentially what they are asking you.” – Zoë Barry, Founder/CEO, Zingeroo, Inc.


On the top skills they look for in a board member

“Investors are going to trigger putting a board together- getting a deal done is about control and who will have control. Boards want shared control, when building out that board, I’m looking for a person that will ask the only thing that matters, ‘How can I help?’”  – Zoë Barry, Founder/CEO, Zingeroo, Inc.

“You must figure out where you want to take the company and determine who can help you get there. We want people from other software companies, we want someone with a very strong ‘PEOPLE’ background, and we are looking for strategists. They need practical experience to make sure they can help you when times get tough and help you open doors.” – Yogesh Gupta, President and CEO, Progress Software

 “Board members have superpowers and kryptonite. One person may have run finance at scale as their superpower, but they may not have experience in customer success or marketing. You must narrow into what is their true power and does that fit into the rest of the mosaic of the board. Oftentimes, people think they are awesome at everything, but it can’t be that. My coaching would be to ask you, where do you bring something uniquely powerful to the board?” – Chris Comparato, Chairman & CEO, Toast

“That mosaic is formalized into a skills matrix; you look at that matrix and say, ‘Where are the gaps?’ You are required to have financial experts on the board at public companies, you must have maturity. You should and must have diversity. You should need people that understand your industry. You should have tech experts and sales and marketing experts. You must publish the skills matrix in your annual report to prove to the shareholders that you have your bases covered, always think about the mosaic. For candidates on the other side trying to get on a board, you want to understand, ‘What is the company looking for?’” – Jim Heppelmann, CEO, PTC

“A trend I’ve seen over the last 10 years public boards in general have transitioned to specific spikes of expertise; tech, cyber tech, security, sustainability, etc. Having a skillset that the board is lacking, or needs is very important to get noticed, having spikiness in a skillset creates a lot of opportunities.” – Marla Beck, Founder, Bluemercury 


On their thoughts on limits on boards & if they have ever left to open a spot to the board.

“More importantly than tenure, it’s continually making sure the board is the right board for your business. Critically evaluate yourself and make sure the matrix is right. The matrix changes, if your strategy changes you must ask, ‘do I have the right board?’ It is not about the time on the board that someone has spent, it is if the individual is still relevant.” Yogesh Gupta, President and CEO, Progress Software

 “We have discussed term limits and decided it’s a bad idea. When you put out your proxy to solicit board candidates, we are now are beginning to frown on directors that have long tenures. If you’ve been on a board for 12 years, you might start aligning with management, but you will have some people that have been there for 12 and some that have been there 1 and it’s not a problem- a mix is good.” – Jim Heppelmann, CEO, PTC

“The board must perform; it is not an entitled position with guaranteed tenure. The CEO is evaluating them constantly to see if they are performing. You have to make sure you are adding value in terms of your expertise, if not you should be questioning what your role is on the board.” –  Chris Comparato, Chairman & CEO, Toast

“ When a board is getting ready to make a change, you want to know the mosaic of the board and I won’t put someone on the board until I’ve known them for a year, or I’ve had at least 3 disagreements with them. There are real decisions that impact growth in earlier stage companies, you need to have established the relationship early on.”  – Zoë Barry, Founder/CEO, Zingeroo, Inc.


On board diversity

“We needed to add diversity and transition to a diverse group, you are looking for someone with the right skill set and someone diverse to bring perspectives. Look at who your client is and say, ‘Does my board align with that as well?’” – Marla Beck, Founder, Bluemercury 

“When creating a board, independent investor diversity is a constant topic. Look at how to build a diverse board that can challenge each other and takes all communities into consideration.” –  Chris Comparato, Chairman & CEO, Toast

“It is becoming a law- at least 2 diverse candidates or 20% that practically speaking you have to aim for on a board. We have to disclose that as a public company.” – Jim Heppelmann, CEO, PTC


On how to get on a board

“Don’t just call headhunters, try to go to events where you can meet them in person, personal referrals are best if you can get a referral.” – Marla Beck, Founder, Bluemercury 

“SPVs can get angel investors to pool money – commit to $2500 per year, it’s a way to begin to build your network and see the issues entrepreneurs are facing. If you are seen as an expert, you can get a startup board seat and then one day someone will pay you to be on the board. Start with a 3-person board and start building relationships with established board members who can pull other people in—think about being an advisor.”  – Zoë Barry, Founder/CEO, Zingeroo, Inc.

Try to get exposure to the board before joining. Great boards will have their senior management teams as part of their presentations. Let your CEO know you are interested in joining a board, a great CEO will help their teams grow and develop and they can help give you that development opportunity.” – Marla Beck, Founder, Bluemercury 

 “Your CEO should be your champion, there is no reason why not. Get them on board early on and ask them for advice and help networking.” – Yogesh Gupta, President and CEO, Progress Software


On expected transferable skills for board members and new skills to learn in advance as opposed to on the job

“First, being amazing at teamwork and matching our company’s values. We try to scrub board members to make sure they come in with no ego, they show themselves in how they interview. Second, thinking strategically, they need the ability to see down the road and know how to think ahead and help your business with long-term problems.” Chris Comparato, Chairman & CEO, Toast

“Don’t play games, disagree without being disagreeable.”  – Zoë Barry, Founder/CEO, Zingeroo, Inc.

 “Character and values have to be a very high bar!” – Yogesh Gupta, President and CEO, Progress Software

“The skills you have are what will attract us to you. You will have to think through how this company will be different. If someone invites me to be on a board, I will look very hard at why they want me and why I want them. At a minimum, ask if you will bring value to the company and will the company bring value to you.” – Jim Heppelmann, CEO, PTC


The fall sessions of Board Ready Bootcamp are wrapping up. Stay tuned for more key takeaways from our rockstar lineup of speakers, and learn more about how to join future cohorts of the program.


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