How Startup CEOs Can Protect Their Interests When Stepping Down to Executive Roles

 

July 2026 Edition

We are now into summer. Hopefully, you and your family had a most enjoyable July 4th / Independence Day holiday this past weekend, celebrating the 250th anniversary of American Independence! and perhaps you might even be able to continue with a further family vacation. Whether cookouts, picnics, clambakes, time at the beach and seashore, or the lakes, swimming, sailing, biking, walking, hiking or out at the golf links or taking in a ballgame at Fenway Park, I hope you and yours are enjoying summer fun.

For me, I am back in the office after a short vacation trip with three friends to Maine. We enjoyed a barn-burner of a ballgame where the Red Sox farm team the AA Portland Sea Dogs, closed a 9–0 deficit to get to 9–8 before losing to the Altoona Drive (farm team of Pittsburgh Pirates) — lots of home runs including a grand slam HR on each side. We also enjoyed great dining, beginning with our first lunch at the Maine Diner in Wells, https://mainediner.com/menu/ , where I enjoyed the “The Jim Nantz” special, hot lobster roll plus a cup of their award-winning Seafood Chowder. Our great dining experiences, continued to our last lunch in Perkins Cove, Ogunquit, where at old favorite Barnacle Billy’s, https://www.barnbilly.com/barnaclebillys-menu I enjoyed a scrumptious 1 -1/2 pound boiled lobster and, with my friend Howie Sholkin, shared a delicious whole-belly friend clams appetizer.

On the local sports scene, it’s been something of a case of bad to worse. The Red Sox after a recent spurt, with their surprising 4-win sweep of the Yankees, and 3-game win sweep of the Angels, are still 8 games below .500 and remain mired in last place. Then, the Celtics surprised us with even worse news — the trade of Jaylen Brown, my favorite Celtics player, a league standout and the team’s 2026 MVP, in a lopsided desperation move, a Mookie Betts-like salary dump, trading Brown within our division to the 76ers. In the words of old Sox announcer Ned Martin, “Mercy!”

On a brighter sports note, I have enjoyed watching and following the World Cup. Across the street from our office building at 101 Federal Street in downtown Boston, there is a great viewing area, with a huge TV screen and seating for 100, surrounded by the food court with 20 eateries at High Street Place Food Hall https://www.highstreetplace.com/ . It was there that I had some fun encounters with inebriated members of the “Tartan Army”, fans of the Scotland World Cup team, many clad in their kilts and even some with their bagpipes, and other fans of Norway who demonstrated their rowing used to rouse their team to success. I’ve also had fun rooting for the host USA team. Until the recent controversy and subpar team performance in our 4–1 loss to Belgium Monday night in Seattle in the Round of 16, this had been one of the best USA men’s team World Cup showing since the first World Cup almost a century ago in 1930 when in a vastly smaller field the US advanced to the semifinals and finished 3rd overall. Sad ending. Even more, I’ve enjoyed rooting for underdog teams from across the Globe, including upsets of great traditional soccer powers, Germany and Netherlands, and the great effort of tiny Cape Verde (Cabo Verde) with the team’s tenacious 40-year old goalkeeper , Josimar José Évora Dias, commonly known as Vozinha. In the classic match of Cape Verde vs Argentina, Vozinha made several excellent saves including a point blank save against Argentine legend Lionel Messi. https://www.youtube.com/watch?v=1amv62-LOoc The Cape Verdeans came from behind to tie 2–2, pushing the Argentines to the brink before finally going down 3–2 in the 15-minute extra time. If you have gotten the chance to watch, hope you too have enjoyed this event.

As for Newsletter items, a week ago, IVYEXEC, the career advancement website published an article I wrote on challenges faced by Founder/CEOs who can become victims of success and what protections you should consider if you or a colleagues faces this dilemma. My July 2026 newsletter also offers two other professional article links, these are to two earlier articles I wrote in items #3 and #4. The first article is on covenants to safeguard non-financial executive pay, when you are taking a job mainly for reasons other than cash or equity compensation, published by CEOWORLD magazine in 2021 but still relevant. The second article discusses benefits, but also potential risks, of Board of Director service by C-level and senior executives, published CEOWORLD magazine in 2019 but also still relevant today. There is also a special offer as item #5, an Executive Issues Law Diagnostic. I hope some of these items might be of benefit… and my best wishes to all for the rest of July!

1. Protections if you face the Founder CEO Dilemma

Are you a victim of your own success? Do you face the “Founder’s Dilemma”: A Founder CEO after a successful launch, now being pushed by the VCs to step aside for a “professional CEO” to lead the scale up to the liquidity event. My new article published a week ago, on July 1, in the IVYEXEC, career advancement website, offers advice and key protections that might benefit you to navigate the shoals of this situation… Read the Article Here

2. Work with CEOs, C-Suite and Senior Executives, exclusively.

Robert Adelson is an attorney specialized in the representation of CEOs, C-level and senior executives. He no longer represents companies or employers. Learn about Robert Adelson’s work with CEOs, C-level and senior executives to advise on and improve job offers, employment contracts, stock, RSUs, options, bonuses and other executive compensation matters, plus advice and aid on issues of wrongful termination, severance, exit terms, retention, change of control, other executive issues and more … More Details Here

3. Contract Covenants to Safeguard Non-Financial Executive Pay

As a CEO, C-level or senior executive, have you ever been paid in ways other than salary, bonus or equity? Sometimes you sacrifice those and even take further risks for “non-financial executive pay.” Those can be assignments in a new field, making key contacts, gaining skills exposure in your industry. My article published by CEOWORLD in May 2021, and still relevant today, gives two examples of a CFO client who wanted to lead his first IPO, and another client who wanted to be a first time CEO, and discusses the special contract covenants I drafted for them and others to safeguard their non-financial executive pay, to give them the best chance to achieve the career advancement for which they were making real financial and family sacrifices… Read the Article Here

4. Executive Service on Corporate Boards of Directors

Are you a CEO or other senior executive who has been offered the opportunity to serve on corporate Boards of Directors in your own company and another company? My article published by CEOWORLD magazine in 2019 but still relevant today, advises on benefits, compensation, potential liabilities and needed protections to put in place for Board service. Read the Article Here

5. 7/2026 Offer: Good until July 24th

This 2-week value-packed offer, is as a way to get introduced to my law work: an Executive Issues Law Diagnostic — this offer is good through 7/24/26. More Details Here

It’s always a pleasure to get back in touch with you and other clients, friends, and colleagues. I hope the links and information provided will be useful to you and that there will be an opportunity for me to work with you on legal matters in the near future.

Let’s keep in touch!

Best regards,

Rob

Robert Adelson

*Adelson & Associates, LLC
Executive Employment Attorney
101 Federal Street, 19th Floor
Boston, MA 02110
(617) 204–5601 Law Firm
(617) 204–5602 Direct
(617) 204–5604 Fax
E-mail : rob@attorneyadelson.com
Blog: https://robadelson.wordpress.com/
Twitter: @AttorneyAdelson
LinkedIn: https://www.linkedin.com/in/robert-adelson-b8a1557/
Website: www.executiveemploymentattorney.com

Note on Adelson & Associates, LLC:
* Robert A. Adelson is the Principal of Adelson & Associates, LLC. For fifteen (15) years, from October 2004 through December 2019, Robert Adelson practiced law and referred legal work to associates of his, trusted and experienced colleagues, as a partner of Engel & Schultz, LLP. In December 2019, the lead partners of the firm announced they would go into semi-retirement, go their separate ways, and the office lease would expire in January 2020. In response, Robert Adelson formed Adelson & Associates, LLC in December 2019 and commenced the new firm’s operations on January 1, 2020, with the new firm taking over, on that date and going forward, all current Robert Adelson clients, matters and operations, as well as all referral of legal work to associates of Robert Adelson. Since 1/1/2020, the firm’s offices have been and remain at 101 Federal Street, 19th Floor, across the street from the pre-2020 offices at One Federal Street, 21st Floor, in Boston’s Financial District.

Executive Contract Negotiations for Life Sciences Executives

On Wednesday October 9, 2024, the executive career advancement website IvyExec published an article I wrote, “Executive Contract Negotiations for Life Sciences Executives.

This article was designed for CEOs and other C-Suite, VPs or other senior executives in Medical Device, Biotechnology and other life science companies who, when negotiating a new job offer or employment contract or terms of executive compensation, need to give attention to essential employment terms in these fast growing and changing industries.

My article indicates how in these negotiations, the executive should seek key executive employment terms in the following important areas:

• Signing bonus to at least make you whole for anything you are giving up,
• Performance targets geared to your type and stage of life science company and its exit goals,
• Equity in scope and form matched to your position, stage of company and potential tax issues
• Relocation and other expenses (e.g. maintaining your M.D. license) again to keep you whole when you change companies.

The article also discusses executive severance terms and triggers for your protection in case changes necessitate you to change companies in the future.

To see my full article, go to LINK: https://ivyexec.com/career-advice/2024/executive-contract-negotiations-for-life-sciences-executives

or my website, go to LINK: https://www.executiveemploymentattorney.com/executive-contract-negotiations-for-life-sciences-executives/

IvyExec hosts articles and webinars from experts in the career, leadership, and business spaces who wish to share their knowledge with our audience. In April 2021, I was invited to write for IvyExec since it seeks original content on the topics of career development, leadership, and business strategy as it applies to senior-level and C-Suite professionals. IvyExec blog posts and webinars are shared with its community of more than 2 million members on its website, in its newsletter, and on its social media channels. https://www.ivyexec.com/career-advice/write-for-us/
IvyExec claims a “Community of 2.5M+ Leaders”. See also — https://www.ivyexec.com/

It is my hope that this article will be helpful to CEOs and other senior executives in the medical device, biotechnology or other life science industries who are negotiating new executive job offers, employment contracts or executive compensation packages and should pay attention to the essential contract terms discussed in my article.

If you or any colleague of yours has a need in this area, please do reach out to me at rob@attorneyadelson.com or call 617–875–8665.

Key Terms to Negotiate in Your Next Executive Job Offer

Two weeks ago, on Wednesday October 25, 2023, the executive career advancement website IvyExec published an article I wrote on “Key Terms to Negotiate in your next Executive Job Offer”.

When you receive a job offer letter, how do you evaluate it? Do you accept the terms “as is” or do you negotiate? You do a great job negotiating deals for your company but do you always do as well when representing yourself?

This article explores the situations in which you negotiate the employment job offer, the terms you should focus on and their ramifications, and how an executive employment agreement attorney can help you.

Often CEO and senior executive recruits have considerable bargaining power. The employer wants and needs you. You may never be in a better position to negotiate further than you are at the moment of the job offer.

Assuming you get the salary and target bonus you are looking, there is still an awful lot on the table. Many of these items may be far more important than salary, including these key items fully discussed in my article:

• Signing Bonus
• Equity terms
• Equity Structure / Taxation
• Relocation
• Reliance
• Severance terms

Even if this is your only job offer, one at you must take, these terms are just too important to accept them “as is” without at least some effort to structure terms that don’t change the essential deal but still offer you important protections.

Sometimes just a word here or there, or an extra clause added by a skilled attorney can make an enormous change for you in realizing the benefit of your bargain or enabling you to leave a difficult situation you did not anticipate.

To see my full article, go to LINK: https://ivyexec.com/career-advice/2023/key-terms-to-negotiate-in-your-next-executive-job-offer

or my website, go to LINK: https://www.executiveemploymentattorney.com/key-terms-to-negotiate-in-your-next-executive-job-offer/

IvyExec hosts articles and webinars from experts in the career, leadership, and business spaces who wish to share their knowledge with our audience. In April 2021, I was invited to write for IvyExec since it seeks original content on the topics of career development, leadership, and business strategy as it applies to senior-level and C-Suite professionals. IvyExec blog posts and webinars are shared with its community of more than 2 million members on its website, in its newsletter, and on its social media channels. https://www.ivyexec.com/career-advice/write-for-us/

IvyExec claims a “Community of 2.5M+ Leaders”.

See also — https://www.ivyexec.com/
​

If you or one of your colleagues is a CEO or senior executive who has received or expects to receive a new job offer, I am glad to assist. Please do reach out to me at 617–875–8665 or rob@attorneyadelson.com 

Becoming a Remote C-Suite Executive – Opportunities & Employment Terms to Negotiate For

Eleven days ago, on Monday July 27, 2023, the executive career advancement website IvyExec published an article I wrote on “Becoming a Remote C-Suite Executive – Opportunities & Employment Terms to Negotiate For”.

As we emerged from the COVID-19 pandemic, remote work has become a fact of life for almost all businesses. Many executives are now working from home offices or suburban satellite offices and participate in meetings and conferences via online communication tools like Zoom. As a result, there is a growing trend of CEOs and C-suite executives interviewing for and assuming new positions without having to leave their homes or nearby home offices.

My article was designed for CEOs, C-level and senior executives, to offer advice and legal terms to seek and negotiation strategies related to remote work.

The article offers illustrations of how remote zoom meetings are aiding non-profit groups and client development, and then moves to how those same techniques are aiding C-level and senior executives conducting nation-wide job searches for new executive positions.

Then, my article suggests techniques to build a comfort level with prospective employers, for those executives who would like to take up an executive employment opportunity as a remote CEO or C-level executive, including the following negotiation strategies:

• Negotiate initial consulting to get to lead to your next CEO job offer;

• Negotiate for temporary relocation to build company comfort level;

• Use hazards of air and distance travel to reduce on site presence even with temporary relocation;

• Make executive compensation and equity concessions now to gain the remote position, with the expectation of being made whole in a later retention agreement;

• Assure your remote contract provides requisite online connectivity and necessary tools to enable your remote operation.

To see my full article, go to LINK: https://ivyexec.com/career-advice/2023/becoming-a-remote-c-suite-executive-opportunities-employment-terms-to-negotiate-for or my website, go to LINK: https://www.executiveemploymentattorney.com/becoming-a-remote-c-suite-executive-opportunities-employment-terms-to-negotiate-for/

IvyExec hosts articles and webinars from experts in the career, leadership, and business spaces who wish to share their knowledge with our audience. In April 2021, I was invited to write for IvyExec since it seeks original content on the topics of career development, leadership, and business strategy as it applies to senior-level and C-Suite professionals. IvyExec blog posts and webinars are shared with its community of more than 2 million members on its website, in its newsletter, and on its social media channels. https://www.ivyexec.com/career-advice/write-for-us/

IvyExec claims a “Community of 2.5M+ Leaders”.

See also – https://www.ivyexec.com/

It is my hope that this article on opportunities opening up across the US to CEOs, C-level and senior executives for remote work, originally inspired in 2020 by pandemic necessity, remains timely for many and will be of benefit. Hopefully, the topics I discuss including to conduct nationwide job searches, to interview and take positions in desired urban centers and also in more others locations, and to do all that without the need to even leave your home office or local satellite office, and finally, the chance to work remotely and effectively and to negotiate the right terms to secure this desired employment – will be of benefit to the CEO, C-level and senior executive clients I represent. Feel free to share this article. If you or any colleague of yours has a need in this area, please do reach out to me.at rob@attorneyadelson.com or call 617-875-8665.

Essential Employment Terms for Female Executives

Ten days ago, on Monday June 26, 2023, the executive career advancement website IvyExec published an article I wrote on “Essential Employment Terms for Female Executives”.

Despite significant advances in employment laws, gender inequality remains an area of both concern and controversy. Women continue to lag behind men, even at the CEO, C-suite and senior executive level, when it comes to executive compensation, opportunity for advancement, job status and equity sharing, to name just a few.

Many women still have to prove themselves as trail blazers for their gender in all-male executive management teams that still operate as the “old boys club” with a locker room mentality toward women.

This article discusses hurdles faced today by women with regard to

• Hiring — achieving equal pay, benefits and other key terms in hiring
• Change of Control — achieving equal treatment for contributions made that have brought about a successful exit and change of control for the company
• Harassment & Termination — Circumstances where despite their professional attitude and achievements, women are not judged on merit, but instead face gender-based workplace harassment, threatened and even actual employment termination.

In each instance this article discusses not only these circumstances but also actions for women CEOs and senior executives to take to protect their interests, obtain their proper rights and benefits, and continue their path of career advancement.

To see my full article, go to LINK: https://ivyexec.com/career-advice/2023/essential-employment-terms-for-female-executives

or my website at https://www.executiveemploymentattorney.com/essential-employment-terms-for-female-executives/

IvyExec hosts articles and webinars from experts in the career, leadership, and business spaces who wish to share their knowledge with our audience. In April 2021, I was invited to write for IvyExec since it seeks original content on the topics of career development, leadership, and business strategy as it applies to senior-level and C-Suite professionals. IvyExec blog posts and webinars are shared with its community of more than 2 million members on its website, in its newsletter, and on its social media channels. https://www.ivyexec.com/career-advice/write-for-us/
IvyExec claims a “Community of 2.5M+ Leaders”.

See also — https://www.ivyexec.com/

It is the goal of this article and my work in this field to aid women CEOs and senior executives in facing these special challenges when they arise and overcoming these challenges while keeping their careers on the upward trajectory. If you or any colleague of yours has a need in this area, please do reach out to me at rob@attorneyadelson.com or call 617–875–8665.