The Executive Chairman Starter Kit

You’re the CEO and Chairman at your company, OR you’ve been invited to sit on a Board as an independent member….and you’ve decided to take a more active Board role as Chairman or Executive Chairman (this could be the result of the CEO’s or the Board’s decision to bring in a separate Chair). In all cases, it’s a great opportunity, but being the Chair isn’t just a title or figurehead…it comes with a bit of responsibility.

Just to establish a baseline – I was the CEO of Janrain, a PE-backed company recently acquired. I have been the Chairman of the Board (and CEO) of 4 companies, a Board member on an additional 3 companies (where I was the CEO but not the Chair), and involved with 2 more companies as an independent Board Member. Of my Board positions, I’ve been involved in 5 acquisitions (4 of which I led).

Executive Chairman Roles

A chairman doesn’t typically play an active role in the day-to-day operations of a company. They sit on the board of directors and serve as its head. The shareholders are the one’s in charge of electing individuals to this role, as well as others on the board.

An executive chairman (EC), on the other hand, will make themselves available to help in some of the day-to-day in the company, but the extent of their role is dependent on how the company structures itself.  The EC role can vary depending on the company and the EC’s time commitment. However, it’s safe to say that they make themselves more available to the CEO and the company in general.

Relationship between Chairman & CEO

Lets stay focused on the Executive Chair role (vs. just Chair) for now. An executive chairman (EC) is a pretty interesting position. For one, executives of the company report to the CEO, seeing as the CEO is the head of the company. So, believe it or not, the EC essentially reports to the CEO as an executive resource. But, that being said, the Executive Chairman is also considered as the boss of the CEO (the CEO reports to the entire Board who act collectively as his or her “boss”).

Let’s use Eric Schmidt being named executive chairman of Google in 2011 as an example. He previously held the position of CEO but he stepped down and handed the reigns over to Larry Page. As an executive chairman he acted as adviser to both co-founders Page and Sergey Brin.

In summary, as an EC, you are: 1) a CEO-coach, 2) an executive team adviser, and 3) a leader of the Board of Directors (who, in turn, act collectively as the “boss” of the CEO).

Day One as an Executive Chair

So here’s what I would recommend to my peers if they were to take on an EC role. I’ll call it my “Executive Chairman Starter Kit” – and I have to caveat that, as an EC, you might find that the CEO has some, a lot, or a little of the following already:

  1. Establish a CEO Management System
  2. Ensure Investment Thesis Alignment
  3. Perform a Real Issues Inventory
  4. Track and analyze your KPIs
  5. Review your 5yr Strategic Plan
  6. Kick off a Senior Team Personality Assessment / Annual Review
  7. Create Your Board Schedule and Agenda

Let’s talk briefly about each of these.

CEO Management System

My own management system for the businesses that I run will include the following below. It’s how I establish structure around the chaos that all CEOs experience in high-growth companies:

  1. CEO Calendar (the meetings you lead and attend regularly)
  2. BOD Calendar (not just the quarterly schedule, but themes/focus by quarter)
  3. Senior Team Weekly “Roundtable” Meetings (real issue definition & resolution)
  4. Senior Team Bi-Weekly 1:1s (a purposeful agenda and questions you need to drive to add value)
  5. Quarterly Business Review (QBR)
  6. Quarterly Objectives (for you, your team, and ultimately the company)
  7. Board Meetings (overall agenda, information packet, open/closed sessions, the process around it)
  8. Shareholder Meetings (status reports, “earnings calls” for all critical investors)
  9. Company BI/KPI/EPM Dashboard
  10. Annual Strategic Planning & Budgeting Process
  11. Information Architecture (where and how does your team share their data)

So, as an EC, you might sit down with your CEO and see where they are on this list.

Aligning with the Investment Thesis

The common objective as the CEO (and something a Chairman can help frame) is to create shareholder value by improving business performance according to the investment thesis. The last item (the investment thesis) is an important one because it’s where the CEO and his/her investors’ alignment starts. Then investor-CEO alignment continues with a common view on the “from” and “to” of key metrics over time (essentially the pace of business performance), and ultimately the target shareholder value. Let me be more specific with a few detailed questions I ask the CEO:

  1. How much capital are your investors willing to continue to invest? Did they put in $20M and reserve another $20M? Will you need to finance a line of bank debt, expand your existing line, add to the syndicate of investors, or simply rely on an inside round before getting to cash-flow breakeven?
  2. Are your capital resources meant to support the business for 3 years, 2, or just 1?
  3. What are the expectations on valuation, dilution, etc. on the follow-on rounds? Would your investors prefer that you get to cash-flow breakeven with the money you have (to reduce dilution), or is there an expectation that another $50M will be invested and the corresponding dilution is built into their models?
  4. What are your investors’ target returns in Cash on Cash (CoC) and Internal Rate of Return (IRR)? Where is your investment community in terms of the lifecycle of their fund? Do you have 7 years to produce results? Put yourself into your investor’s shoes (and understand the IRR calculation).

In my last company, I set pillars for the business based on this discussion and answering the above questions. Here were my key pillars:

  1. Preference was to achieve an outcome with the existing capital (no more $ raising).
  2. We believed that we had enough capital to last 3 years (do what you need to within that timeframe).
  3. The CoC target was >= 3x; and IRR target was >=40% (ok, yes, a transaction by year 3, ideally with this level of performance)

I had “dry powder” to expand the most recent investment, and I had existing investors willing to syndicate new investors…but those were “plan B” or “plan C” activities. “Plan A” was exactly what we did….we exited within 3 years at 3x CoC and 44% IRR. It wasn’t an outcome that “just happened”. It was an outcome that we architected based on investor-CEO alignment. As the EC, you might see if you can facilitate this understanding.

Real Issues Inventory

With every company that I lead, I like to do an “inventory” of the real issues. I’ll define a “real issue” in a minute. I address real issues that I’d broadly categorize into two buckets: 1) the perspective of each of the business functions (what does each area of the business need to do, to positively disrupt?), and 2) the overall perspective of the business (what top 3 issues cut across all business functions)?

Now, here’s my definition of a “real-issue”:

  • A topic that would make your stomach linings churn, if brought up as a team
  • Something that you are uncomfortable talking about (especially as a team)
  • Event(s) which are affecting you, your staff, the Company negatively

Why perform a “real-issues” inventory?

  • Teams (companies) fail based on process (team dynamics) not necessarily content (what is actually being talked about). So you need a process / venue that helps you address real issues
  • Every team “hits a wall”. Great teams work through the “real issues”.
  • Every “real issue” that has the potential of “blowing the team apart” is exactly what makes it stronger.
  • Reality always wins. It’s our job to get in touch with it.
  • There are no secrets in teams, just dysfunctional dynamics thinking so.

So once you do an initial inventory of the top 3 real issues cutting across the business, you can then dive deeply into each of the business functions, flushing out a detailed list of real issues. I like to perform workshops and address the issues – putting together a plan to resolve each of them. And you probably guessed it, a CEO should perform a real issue inventory every quarter as part of your Quarterly Business Reviews! So, as an Executive Chair, this is an exercise worth facilitating at least once with your CEO.

Inventory your KPIs

What are the top KPIs in each business function? What is your current measurement of each of those KPIs? What are your targets for steady-state for those KPIs? All great questions. As I reflect on this exercise, I’m looking at my own list of >300 KPIs across the business. >300 means that, obviously, not all are meant to be discussed on a monthly basis. But a detailed list of KPIs can roll up up to a “top 3 KPIs” per business function, and then a “top 3 KPIs” for the entire business. I’ll dedicate a blog on my sanitized list by department for reference later. For now, the EC can collaborate with the CEO on an “executive Dashboard”….so that we’re not driving blindly.

Review your 5yr Strategic Plan

Each year, I like to perform a “painted picture” of the future. Of course, as part of your budgeting cycle, you need to know what next year looks like. However, next year should be a part of an overall 5-year plan. So how should you partner with your CEO on this exercise?

4Q is a planning quarter. Ideally, you head into January of a new year (assuming you have a fiscal year that matches a calendar year) with a clear view of next year’s budget. In fact, my first Board meeting of the year formally approves that budget. Thus, ideally, you will need to have an informal head nod by board members in December preceding your new budget year approval.

A new budget year needs to fit into a broader picture. The broader picture is your 5-year strategic plan, and that 5-year strategic plan needs to align with the investor expectations we already discussed in “Aligning with the Investment Thesis”. I’ll spend some time on this topic separately as well. For now, the EC needs to help facilitate both the 5yr strategic plan update, and next year budget process with the CEO.

Kick off a Senior Team Personality Assessment / Annual Review

Ok, you might not be a fan of Myers Briggs, or DISC, or an equivalent personality assessment. I’m a fan of knowing how to get to “high performing team status”…and doing so is hard without understanding who your senior team is, and how they think and operate. I use Myers Briggs to baseline my staff, and then I ask six other probing questions of each team member.

I put on my MBTI® Certified Practitioner hat (yes, I’m certified to interpret the results of MBTI assessments). I do this in order to understand my team’s personalities and how they interact. I can also take this to the extreme, and profile my entire company, providing them the benefit of knowing the results of their assessment, but also learning about what it means when interacting with others. It starts a dialog, ultimately helping your staff “put themselves into other people’s shoes”.

As an EC, you should work with your CEO to perform a first-time assessment, but then to turn it into an annual review of the senior team – including the CEO themselves. I have a framework that makes Board feedback consistent, year to year.

Create Your Board Schedule and Agenda

Last, but not least, the Chair will work with the CEO and others on the Board to establish a Board process. The schedule and agenda are outputs of a process that includes elements such as:

  • Board meeting open session vs. closed session.
  • Board meeting strategic agenda items: “Major” and “Minor” topics to be covered at each BOD meeting.
  • Proactively giving Board members “homework” ahead of meetings.
  • Using your QBR as an input to your Board meetings.
  • Typical “Board package” (primary and backup materials)
  • Strategic workshops with your Board (ad-hoc, quarterly, or annually)
  • Board member “skip-levels” with individual senior team members, managers, and individual staff

This isn’t a small project. The more you invest, the more you can gain from the value of your “extended team” of BOD members. Again, this is a topic by itself worth spending time to detail.

  • Janrain (2016-2019): Board Member & CEO*
  • Infochimps (2012-2013): Chairman of Board & CEO*
  • StackIQ (2009): Board Member & CEO*
  • Eyespot (2005-2008): Chairman of Board & CEO*
  • Integral (2005): Chairman of Board & CEO
  • INCEP (1999 – 2004): Board Member & CEO*
  • Quantiply (2012 – 2019): Board Member
  • RadarFirst (2006 – 2018): Board Member*
  • GreenEdge (2007 – 2010): Chairman of Board & CEO


Jim Kaskade

Jim Kaskade is a serial entrepreneur & enterprise software executive of over 36 years. He is the CEO of Conversica, a leader in Augmented Workforce solutions that help clients attract, acquire, and grow end-customers. He most recently successfully exited a PE-backed SaaS company, Janrain, in the digital identity security space. Prior to identity, he led a digital application business of over 7,000 people ($1B). Prior to that he led a big data & analytics business of over 1,000 ($250M). He was the CEO of a Big Data Cloud company ($50M); was an EIR at PARC (the Bell Labs of Silicon Valley) which resulted in a spinout of an AML AI company; led two separate private cloud software startups; founded of one of the most advanced digital video SaaS companies delivering online and wireless solutions to over 10,000 enterprises; and was involved with three semiconductor startups (two of which he founded, one of which he sold). He started his career engineering massively parallel processing datacenter applications. Jim has an Electrical and Computer Science Engineering degree from University of California, Santa Barbara, with an emphasis in semiconductor design and computer science; and an MBA from the University of San Diego with an emphasis in entrepreneurship and finance.