How to Get on a Board of Directors (and the Portfolio Life That Should Come With It)
Written By: Ryan Morrison
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The most consequential career advice Tom O'Toole received didn't come from his CEO or a recruiter. It came from a board placement advisor he hired two years before he retired from United Airlines, who told him plainly: get your first public company board seat before you leave your corporate role, or you probably never will. Tom listened. Over the decade since stepping back from United, he has served on four public and four private company boards, worked as a McKinsey senior advisor, and spent six years as Associate Dean for executive programs at Northwestern's Kellogg School. The work to build that portfolio started before he left the building.
Tom O'Toole was Chief Marketing Officer at both Hyatt Hotels and United Airlines, where he also ran the Mileage Plus loyalty program. That program became publicly visible during COVID, when airlines pledged their loyalty businesses as loan collateral and Mileage Plus was disclosed at a $22 billion valuation. Since retiring from United, Tom has chaired nominating and governance committees, run director searches, and been on the candidate side of those same searches. That double perspective is rare in the existing material on board placement, and it changes what counts as useful advice.
TL;DR
Get the first one before you leave. Public board placement is a two-year process. Sitting in a senior corporate role gives candidates access and credibility that becomes harder to replicate after retirement.
Networking matters more than credentials. Search firms send nominating committees fifty highly qualified candidates per seat. A sitting director putting your name in the mix is what distinguishes you.
Most LinkedIn board placement pitches are not legitimate. Real retained search firms are paid by hiring companies, never by candidates. Pay-to-play services charging executives are a red flag.
Public-to-private board transitions work. Private-to-public usually doesn't. Different governance norms and a brighter line between board and management on public boards.
Boards are one element of a portfolio life, not the whole thing. Each commitment should answer a different question, and the design has to be intentional.
Table of Contents
Before the Boards: What a $22 Billion Loyalty Program Teaches About Post-Corporate Value
Get Your First Board Seat Before You Leave Your Corporate Role
How Search Firms Like Russell Reynolds and Egon Zehnder Actually Choose Directors
Are Board Placement Services Worth It? What's Real and What's Not
Public vs Private Board Seats: What Changes When You Cross That Line
What Actually Distinguishes Director Candidates: The Skills Matrix and the Audit Committee Chair
Boards Are Great Until They're Not: What Board Service Actually Looks Like
Boards Are One Element: Why a Portfolio Life Has to Be Designed
Frequently Asked Questions
Episode Resources
Conclusion
Before the Boards: What a $22 Billion Loyalty Program Teaches About Post-Corporate Value
Tom's most quoted credential, running United's Mileage Plus program, is also the clearest example of why his advice on board placement carries weight. He knows what makes someone valuable to a board because he was that candidate.
The valuation became public during COVID. Airlines used their loyalty programs as collateral for emergency loans, which forced disclosure of the underlying economics. Skift ran the headline: how is United Airlines' loyalty program worth $22 billion. CFOs paid attention. So did boards.
The mechanics matter for understanding why. Loyalty programs are not customer affinity tools. They are businesses that sell a currency. Tom puts the scale plainly: "Loyalty points are the third most widely used currency in the world. After the US dollar and the euro, the third most widely used currency in the world is actually loyalty points."
The economic engine is the margin between selling miles and redeeming them. When FTD runs an offer that pays five miles per dollar spent, FTD pays United roughly two and a half cents per mile. United books a portion of that as current revenue, sets aside the rest as future redemption liability, and eventually redeems the mile at a cost of around one and a half cents. Multiply the spread by billions of miles transacted annually, and the program valuation is rational. Multiply that across earning partners (banks, hotels, retailers) and it becomes one of the largest hidden financial businesses inside any major airline.
What this has to do with the rest of the post: Tom's depth running this kind of business is exactly what made him a candidate the search firms wanted to place. Boards do not place generalists at scale. They place operators who have run something. The loyalty program experience was Tom's differentiator. (For a deeper read on award programs from a member's perspective, see the Long Angle conversation with Chris Hutchins on award travel at scale.)
That credential is what made the next step work. The next step is what most senior executives get wrong.
Get Your First Board Seat Before You Leave Your Corporate Role
Franchising is where product-market fit has already been proven, leaving execution risk as the only variable a new investor needs to underwrite.
Andy arrived at this thesis not through franchising itself but through angel investing. After the Custom Ink liquidity event in 2019, he started deploying capital into tech companies and found himself consistently frustrated by the same problem. "I got tired very quickly of funding people trying to find product-market fit. I love an entrepreneur. I love a founder. But I really got tired of funding people trying to find product-market fit." What he wanted to fund was execution risk - the question of whether a capable operator could take a proven model and run it well. Franchising is the only asset category he found that is structurally built around exactly that.
A franchise with a proven unit of one is a business that has already answered the hardest question. Someone has run the model in a real market, generated real revenue, established real margins, and demonstrated that the concept transfers. The capital a franchisee deploys is not going toward discovering whether the idea works. It is going toward whether they can execute. That is a fundamentally different bet, and for a professional with operational experience and capital, it is a much better one.
The broader capital structure point Andy makes is equally important. Venture capital has no interest in mainstream businesses. A home services company or a B2B sales franchise cannot raise a Series A. The only path to growth for many of these businesses is either plowing every dollar of profit back in for another five to ten years, or finding a different financing model. Franchising, Andy argues, is that model - not just a business structure and a distribution system, but a way for a proven local business to scale without taking on conventional debt or giving up equity to investors who do not understand the category.
For professionals already deploying capital into private markets, the comparison to Alternative Investments vs. Traditional Investments is worth drawing. Franchise ownership occupies a different part of the risk-return spectrum than PE or private credit, but the execution-risk framing places it in conversation with the same capital allocation logic.
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How Search Firms Like Russell Reynolds and Egon Zehnder Actually Choose Directors
Search firms develop the candidate slate, but the nominating and governance committee chooses the director. Almost every committee starts the conversation with a sitting director suggesting a name to the search firm.
Tom has been on both sides of this process. He has chaired nominating and governance committees, run director searches, and been the candidate. The mechanics he describes are consistent across the major firms: Russell Reynolds, Egon Zehnder, Spencer Stuart, and Heidrick & Struggles. Each maintains a dedicated board practice, with a senior partner running it. The firms maintain extensive databases of qualified candidates, and they curate slates of fifty or more for each open seat.
What gets a name into that slate is not credentials alone. It is networking. Tom describes how his second public company board came together: a sitting director on that board asked the search firm directly, "What about Tom? Did you consider Tom?" The director cannot appoint Tom to the board, but she can ensure that his name is in the hopper at Egon Zehnder, or whichever firm is running the search. That single sentence, delivered to the right person at the right firm, is often what moves a candidate from invisible to shortlisted.
The data backs the pattern. The PwC survey of corporate directors found that personal recommendations overwhelmingly drive director opportunities. Search firms exist to validate and run the formal process. The actual sourcing happens earlier, through the network. A separate survey by the National Association of Corporate Directors found that nearly 70 percent of directors said their board used personal networking or word of mouth to identify candidates for their most recent director nomination.
The practical implication for someone two years from retirement is concrete. Build relationships with sitting directors in your industry. Get to know the senior partners running the board practices at the major firms. Spread the word among auditors, lawyers, and consultants you have worked with at the C-suite level, because they are also part of the network that gets called for references. The work is unglamorous and slow. It is also the work that fills board seats.
Are Board Placement Services Worth It? What's Real and What's Not
Most paid board placement services advertised on LinkedIn are not paths to top-tier public boards. Legitimate retained search firms are paid by the hiring company, never by candidates seeking seats.
Tom's response to the question of whether these services are legitimate: "Color me skeptical." He elaborates: "I am not aware that that is typically a path to top-tier public company boards." His career-long experience is that the call comes the other way. The search firm calls the candidate, after a sitting director or trusted referrer has put the name forward. Candidates do not pay search firms.
The structural problem with pay-to-play services is misaligned incentives. When a candidate is the one writing the check, the service profits from prolonged subscriptions, not from actual placements. Multiple recent industry analyses have documented the rise of board recruiting scams targeting executives, with FBI cybercrime data showing record losses tied in part to executive-targeted schemes. The pattern is consistent: flattering outreach, vague claims of retained searches, and an eventual pivot to a paid service offering — bio rewrites, board readiness programs, or platform memberships running into the thousands of dollars.
There is one legitimate exception worth naming. Some firms are retained directly by companies that want to place their CEO on an external board as part of professional development. That is a real engagement, paid for by the CEO's company, not by the CEO. Tom has seen it work. It is not what is being pitched on LinkedIn.
For someone serious about getting on a public board, the path is the one this post has been describing. Build the network. Develop relationships with the major search firms before you need them. Get a sitting director to put your name into circulation. The candidate-paid alternative is, in Tom's framing, not a real path.
Public vs Private Board Seats: What Changes When You Cross That Line
Public board service requires a brighter line between board and management than private board service, where directors are expected to engage operationally. Going public-to-private is easy. Going private-to-public usually doesn't help much.
Tom has done both. Four public boards, four private. He treats the distinction as substantive, not cosmetic. On a public board, the role is governance. The director sets strategy, oversees risk, approves transactions, and supervises the CEO, but does not direct managers below the C-suite. That separation is enforced by securities law, by D&O liability structures, and by the practical norms of how public boards function. A director who tries to step over the line into operations is creating problems for the company and for themselves.
Private boards operate differently. Directors are expected to be more hands-on. They engage with management on business development, sometimes on hiring, often on operational decisions that a public board would never touch. Tom describes the difference plainly: things that would be "way over the line in a public company board" are "expected of you on a private company board."
The practical implication for someone planning their first board seat: aim for the public seat first if you have the option. The same person who served on a public board can transition into a private board comfortably, because private boards welcome directors with public board experience. The reverse is harder. Time spent on private boards does not translate into a credential that gets a candidate placed on a public one.
The ranking matters when planning the two-year search. If a candidate has the credentials for a public seat, the right move is to focus the time on landing one, not to take a private seat as a stepping stone. Private board experience accumulates well after the first public seat is in place.
The Multi-Unit Sweet Spot and the Wealth-Building Math
Every board maintains a skills matrix that maps each director's expertise across functions like cybersecurity, financial management, and risk. The candidates who fill the gap on that matrix are the ones who get placed.
Tom describes the matrix as something he can picture in his head for the boards he serves on. Each row lists a director. Each column lists a skill. A board doing a director search looks at the matrix, identifies the gaps, and tells the search firm what kind of expertise the candidate slate needs to bring. Cybersecurity has been a heavily weighted gap across most boards in recent years. Financial expertise, IT, risk management, and industry-specific knowledge are perennial.
For someone trying to land a first seat, the skills matrix logic is what differentiates the hopeful from the placed. Generic operating credentials matter less than a specific, named expertise the board does not currently have. Tom's framing: "What do you bring to this? Be it financial expertise and so on and so forth."
The single most powerful credential, when it applies, is qualifying as an SEC financial expert and being able to chair an audit committee. The SEC defines specific qualifications for the financial expert designation, and public companies are required to disclose whether they have one on the audit committee. Candidates who can credibly chair an audit committee are scarcer than the demand for them, which materially shortens the timeline and improves the seat options. If a candidate has the credentials to chair an audit committee, that credential should lead the conversation with every search firm.
Most candidates do not qualify, and that is fine. The next-best move is to be specific about what gap the candidate fills. Walking into a search firm conversation with a clean answer to "what board skill do you bring that most of their target boards are short on" is what gets the candidate from the slate of fifty into the slate of five.
Are you navigating what comes after the corporate role?
The decisions that follow a senior career, board placement, allocation, identity, time, are not financial decisions alone. Long Angle Trusted Circles are small, vetted peer advisory groups for members at this exact stage. Eight to twelve people, monthly meetings, fully solicitation-free. The Post-Exit / Next Chapter Circle and the High-Intensity Builders cohort both serve members working through this transition with peers who have done it.
Boards Are Great Until They're Not: What Board Service Actually Looks Like
Board service is rewarding and well-compensated until a crisis hits. At that point directors earn every dollar through weekly meetings, activist defenses, cybersecurity incidents, or financial distress.
Tom's framing is direct: "Boards are great until they're not." He describes one board where, during a crisis period, the directors held meetings every Tuesday and Thursday morning at 7am for months. That cadence is not the norm. It is the part of the job most outside descriptions of board service skip.
The work activates around four common triggers: an activist investor showing up, a cybersecurity incident, financial distress, or a material transaction (announced or unsolicited). When any of these hit, the board's risk obligations to shareholders sharpen. The general counsel typically reminds directors of their fiduciary duty, the cadence increases, and the director's job moves from oversight to active governance under pressure.
A common assumption from outside observers is that visible CEO-board friction means the board failed to act. Tom reframes it. By the time a major transaction is announced, the board has already approved it. If a deal looks irrational from the outside, the relevant question is not why the board didn't stop it. The question is why they approved it. The board's obligation, particularly on questions of value-maximizing transactions, is shareholder value. If the board signs off, they have already concluded the transaction meets that test.
This is the honest version of public board service. The compensation is real. The time commitment in a quiet year is reasonable. When the year is not quiet, directors earn their pay. Anyone evaluating the path should know that quiet years are the assumption built into the comp, not a guarantee of how the job will feel.
Boards Are One Element: Why a Portfolio Life Has to Be Designed
A portfolio life after corporate retirement is not something that happens organically. Each element (boards, advisory work, teaching) must serve a deliberately different purpose, and the question to answer for every commitment is: why am I doing this?
Tom's portfolio is the lived case study. Four public and four private boards across the past decade. Ten years as a McKinsey senior advisor. Six years as Associate Dean for executive programs at Northwestern's Kellogg School. Each piece does a different job.
Boards are the financially material element. The compensation is real, the obligation is real, and the credentialing compounds. Tom continues to serve on Aligned Energy's board and has rotated through others over the decade.
McKinsey serves a different purpose entirely. Tom is direct: "I'm not doing McKinsey for the money. McKinsey serves a different purpose in the portfolio." The role keeps him intellectually current with C-level clients, on real engagements, with stakes that demand current thinking. The work, depending on the engagement, ranges from sitting in the back of a client meeting to presenting to a board. That range is the point. The role exists to keep him sharp, not to pay him.
Teaching at Kellogg, the role he stepped back from at the end of August, was the third leg. It served its own purpose, which Tom defines elsewhere. The pattern across all three is the same: each commitment answers a question that no other commitment in the portfolio answers.
The framing that distinguishes design from drift is the question Tom keeps returning to: "Why am I doing this? Not just because it's cool, not because it's interesting, not because it's, you know. Why am I doing this?" Most senior executives heading into post-corporate life have not answered that question for any of the commitments they accumulate. The result is a calendar full of activity that does not produce a coherent life.
For an audience navigating this transition, the discipline is the same as career design. Define what each piece is supposed to do. Pick the pieces that do that job. Decline the ones that do not. The related Long Angle conversation on what to do after selling your business covers the same problem from the founder side. The decision frame is the same.
Frequently Asked Questions
When should I start looking for a board seat before I retire?
At least two years before leaving a senior corporate role. Tom O'Toole started his board search two years before retiring from United, on advice from a board placement advisor. After retirement, the credentials and access that make you a candidate begin to fade, and getting the first seat becomes materially harder.
How do I get my first public board seat with no prior board experience?
Lead with sitting directors in your network and the board practice partners at Russell Reynolds, Egon Zehnder, Spencer Stuart, or Heidrick & Struggles. Most board appointments come from word of mouth, with surveys consistently showing networking as the single strongest source.
Are LinkedIn board placement services legitimate?
For top-tier public boards, generally no. Legitimate retained search firms are paid by hiring companies, not candidates. Services charging executives upfront fees are a structural red flag because they profit from subscriptions rather than placements.
What's the difference between public and private company board service?
Public boards maintain a clear line between board and management. Directors govern but do not direct managers. Private boards expect more operational engagement from directors, including in business development and hiring. Going public-to-private is easy. Going private-to-public usually doesn't help much.
Do I need to be a CEO to get on a public board?
No, but you usually need C-suite or near-C-suite experience at a substantial company. Below that level, the realistic path runs through smaller private companies first, and a public seat may not be a feasible target. CFOs and senior executives with named functional expertise (financial, cybersecurity, technology) place onto public boards regularly.
Final Thoughts
Tom O'Toole's case study is unusual in that it makes the work visible. Most senior executives who land on public boards describe the path in passive terms. The seat came together. The recruiter called. A friend put a name forward. What Tom describes is the same thing told actively. He hired an advisor two years before he left United. He developed relationships with the senior partners running board practices at the major search firms. He built the network of sitting directors who would eventually put his name in the hopper at Egon Zehnder, Russell Reynolds, and the others. The first seat took years of deliberate work. The second came faster because the first was in place. By the fourth public board, the dynamics had shifted entirely.
The board work is one element. The McKinsey advisory role keeps him intellectually current. The teaching at Kellogg served a separate purpose. Each commitment answers a question the other commitments do not. That is what a designed portfolio life looks like. The alternative, which is what most senior executives default into, is a calendar of activity that does not add up to a coherent post-corporate identity.
For anyone within two years of leaving a senior corporate role, Tom's advice compresses to one line. Start now.
Vetted peers comparing notes on the decisions that come next.
The decisions that follow a senior career do not stop at board seats. Allocation across public and private markets, tax structuring before an exit, time and identity in the next chapter, the candid version of these conversations rarely happens with advisors who are selling something. Long Angle is a vetted community of founders, executives, and investors who compare notes on all of it in a solicitation-free environment. Members come for the peer signal and stay for the breadth.
Resources Mentioned
Subscribe to the Navigating Wealth Newsletter
The 2026 Long Angle Asset Allocation Report
Related Long Angle reading: What to Do After Selling Your Business
Related Long Angle reading: The Top High-Net-Worth Retirement Strategies
Related Navigating Wealth episode: Selling a SaaS Business: What Actually Drives a Strong Exit
Related Navigating Wealth episode: Award Travel: When Points Still Beat Cash
Connect with Tom O'Toole: totoole@me.com
