**by Caitlyn Driehorst**

Caitlyn Driehorst is a financial advisor at RightWise Wealth, as well as the firm's founder and CEO. Caitlyn began her career at the Boston Consulting Group and held strategy roles at MGM Resorts, Capital Group American Funds and two venture-backed wealth startups. She holds a B.A. from the University of Chicago and an M.B.A. from UC Berkeley's Haas School of Business.
Published: February 9, 2025

At RightWise, we are proud that we support “everything in your life with a dollar sign,” now including tax filing via our integrated partnership with tax firm Uprise.

When clients ask us for support with a job offer, we can plug in by helping:

Understand structures for stock compensation
Reviewing benefits packages
Point towards various benchmarking resources; e.g., I’m a big fan of my friend Hari Raghavan’s Fair Offer tool at Autograph
General thought partnership on positioning

But we’re not specialists, and so I was thrilled to meet Sara Perelli-Minetti of Hellos & Goodbyes. Not only do she and I have a lot in common – including overlapping time at the Boston Consulting Group in Chicago, family connections to the military and children nearly the same age – but her “been there, done that” is exactly the missing ingredient I’ve been seeking.

Sara, what was your path towards becoming an executive negotiation consultant?

I didn’t know it at the time, but my feet have been on this path since the beginning of my career. I graduated college right before the Great Financial Crisis and was promptly laid off from my first job. I ended up negotiating a 40% improvement in that severance package – I have to pat 23-year-old me on the back for that one!

Over the following decade, I kept that confidence and negotiated other severance and job offers, even fresh out of MBA where they told you that you “can’t” negotiate a standard offer.

But then I got to see the negotiation process from the other side of the table as I spent 7.5 years at Capital One, promoted into increasingly senior roles in HR, and then similarly as I held a senior HR role at Wayfair and a venture-backed startup. Now I was the one creating and structuring offers or overseeing RIFs, and the opaque world of internal incentives and capabilities opened in front of me.

I’d become the go-to person in all my group chats for all things negotiation, and I realized that not only did I feel such joy in helping people get what they deserve, but I also saw that I was creating real economic value and could turn this into a business.

And here we are! Today, I support negotiations for job offer negotiation, executive contracts, and severance packages.

One reason I wanted to feature your work is how we think about building client net worth. We hold a thorough budget conversation with every household, but all else equal, I’d rather see my client earn another $10,000 rather than cut back on snacks and lattes to save another $10,000. What type of wins have you accomplished alongside your clients?

Earlier this year, I helped a client increase the total value of her package by $140,000. She was transitioning from a Senior Director role at a Series E company to a VP role at a Series B startup. We improved her base salary by $30,000 and increased her equity award by $20,000, secured immediate vesting (waived one-year cliff), and extended her post-termination exercise window from 90 days to a full year. We also negotiated a delayed start date to protect $90,000 in stock vests from her current employer.

I can support these types of increases not only because I’ve been around the block myself and can walk you through prioritization, phrasing and the right level of persistence, but also because I pay for benchmarking services like Carta. My clients can walk in with the soft and hard tools they need.

And the value is so much more than the year-one headline numbers! It’s also how these stair-steps can compound over time.

Oh. We love compounding.

An increase in salary is not just $20,000 today, but also a lift to any subsequent cost-of-living or merit raise, and it resets the benchmark for any future role. Not to mention potential increases for 401(k) contributions, I could go on and on.

Offer negotiation has felt most critical for our clients when we’ve seen leaders going under contract. Their employers are asking for real concessions – enforceable non-competes and non-solicits, for example – and that gives our clients the right to ask for real consideration.

At the same time, it can be overwhelming to swim beyond the shallow waters of “base salary and some vacation days,” and newly-promoted leaders can want to show they are team players. What’s new when you’re entering a contract negotiation? Where is the process unchanged?

You’re correct that most people are familiar with negotiating the upside of their offer. As you become a more-senior leader, you have increased standing and increased need to negotiate downside protection.

Senior leaders can often face much longer time between roles, if only because those very-senior roles are less common in the market. Any given startup may have three directors of marketing, for example, and promotions may open up one of those roles every few years for a new candidate. But that same startup will probably only have one Chief Marketing Officer, and those senior roles also have less turnover.

For my executive contract clients, some downside protection items:

What is your guaranteed severance? Can you negotiate a greater amount if you lose your role for anything other than cause?
If you’re agreeing to a non-compete, does that time period match your severance? If your contract agrees to a twelve-month non-compete but you’ve only negotiated six months of severance, you’re blocking yourself out of your field for six months without pay.

For senior leaders, equity compensation can be a disproportionate part of their total compensation, and here, too, you want to negotiate structures that protect your downside:

What is the vesting schedule? If there’s a one-year cliff, negotiate to waive that. I’ve seen too many people laid off in their first year as part of RIFs and then receive $0 of their equity.
Under what conditions can you sell your shares in a secondary market? Are there any scheduled liquidity events, and will you be able to participate? That IPO can stay “just around the corner” for years, and you may need liquidity.
If options, what is the post-termination exercise window? In most companies, it’s one to three months, which gives you very little time to make a huge decision about whether or not to exercise your options. I always recommend negotiating at least a year, even with the tax implications. I’ve written about this in more detail here.
Senior leaders receiving options should also ask about double trigger acceleration, especially if they work in departments like finance, HR or marketing, which often see job losses in acquisitions or mergers. More here.

It’s great when a client can coordinate with their financial advisor so the two of us can help explain and look out for these complex interests.

“Negotiations” was the best class I took at MBA, and the best advice from that class was “never negotiate on only one item; put as much as you can on the table.” Besides salary and stock, what do you help your executive clients negotiate in their contracts?

I love to see my clients negotiate:

Sign-on bonus
Start date
Title
PTO
Parental leave
Working arrangement / travel schedule
Future compensation reviews or increases
And of course, severance packages, especially if VP+

But just because you can negotiate all of these things doesn’t mean you should. Focus your negotiation on the items that are most important to you. This is why my first step with all of my clients is a deep dive on their priorities. It’s a personalized process.

The job market is soft right now, especially at mid-senior levels in certain parts of tech. How does that affect how aggressively you may push clients to negotiate?

The overall job market is soft, although I am seeing some strong activity in Q1 2026.

First of all, I never want a client to negotiate “aggressively.” The words I like to use instead are, “strong” and “firm.” But how strong and how firm will depend entirely on a client’s willingness to walk away from the offer. Practically speaking, this is usually informed by whether the client is currently employed and how many job offers they have.

So, for example, if a client is long-term unemployed and has only one offer we know they’ll take no matter what, we’re going to do a very soft ask. This might look like one counter with careful framing for other requests.

On the other hand, if a client is currently employed, willing to stay in their job and has multiple offers, we can hold the line on a total cash amount and make a strong case for sign-on bonuses and other pluses.

Regardless of the job market or willingness to walk away, the tone should always be warm and collaborative, never combative, even in severance negotiations. Candidates or employees who come across as lacking respect, entitled or litigious do not, in my experience, see as positive of outcomes as those who take a more collaborative approach. As a consultant and coach, I am a third party who can help reduce the negative emotions. Vent away to me! And then, together, let’s write something much calmer.

What’s the best time for an executive to engage you in their process?

For job offer negotiation, the best time to rope me in is when you’ve progressed into final rounds but before the offer calls. There’s so much valuable information to be gained in interviews. That said, I regularly have clients who call me when they have their offers, and we do just fine!

For severance, the ideal time to engage in my coaching is before you’ve been laid off – though obviously, that can be difficult to know in advance.

It’s very difficult to negotiate severance if you’ve been terminated as a part of a RIF and have no evidence that you were individually targeted; these packages are often take-it-or-leave-it. I’m upfront with people and won’t accept a client where our odds of success are too low.

And how is your compensation structured?

I do my best to keep my incentives aligned with my clients’ and focused on results.

For job offers, I use a success fee and retainer model. My success fee is 10% of negotiated upside of year-one compensation, with a $1,500 retainer due at the start. If a client doesn’t receive any offers, we waive that retainer.

For severance negotiations, I charge the greater of one week’s base pay or a $2,000 minimum fee.

How does your work compare to that of an employment attorney? Where are you distinct, and where do you collaborate?

I am not an employment attorney! I partner with them frequently -- especially on employment agreements or where severance situations may include discrimination -- however, my consultation does not constitute or replace legal advice, and I don't write contract language or edit any legally binding documents.

When I partner with employment attorneys, they focus on legal issue identification, including state-specific requirements, and specific legal language in any written documents, where I focus on holistic negotiation strategy, business rationale for any counter-offers, framing, and employer-facing communication.

Because you pay for my services with a success fee (job offers) or a flat fee (severance) rather than billable hours, you can lean on me for open-ended coaching, brainstorming and thought partnership, whereas you may want to keep time with your attorney more tightly-focused on legal issues. I'm happy to work with an attorney you already know, or I can also help refer or introduce you to someone from my network.

What’s the best way for someone to reach you, if they’re interested in your support for a negotiation?

Head over to my website to schedule a discovery call; there’s also a form to reach me via email.

LinkedIn is also a great way to stay in touch, as I write about negotiations and compensation several times a week and I try to pack in as many practical tips as I can!

**More About Sara**

Sara Perelli-Minetti founded Hellos & Goodbyes to help people negotiate stronger job offers, raises, and severance packages. Her clients regularly see 10-40% increases in total compensation, as well as increased protections for layoffs and favorable stock compensation structures. Prior to starting Hellos & Goodbyes, Sara worked in HR senior leadership at Capital One, Wayfair and a venture-backed startup, as well as consulting roles at the Cambridge Group and Boston Consulting Group. She is trained as a Co-Active coach and holds an MBA from the University of Michigan’s Ross School of Business. Sara lives in Reston, VA, with her family.

Here to help you with your full financial life

Consider working with an independent financial advisor to spot-check your thinking, and place your decisions in the context of your broader financial plan.

Reach out today to meet with a RightWise advisor.

Request an Intro