😎 Equity Offers: Don’t Get Played

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issue #4 | date: 05/21/2025

Editors Note

Hello & Happy Wednesday!

Welcome to our growing community! Whether you're crushing it in delivery, managing high-stakes programs, or building the ops engine that makes everything run, this newsletter is your weekly jumpstart.

We bring you what actually matters in the business of delivery: real job opportunities, career tactics that work, and insights you can actually use.

Today, we’re talking about equity. If someone offers you Stock Appreciation Rights (SARs) instead of actual equity, they're basically handing you a fancy IOU rather than keys to the business. It's a cash bonus with a fancy name, not true ownership.

If you're shooting for meaningful upside, you need to get comfortable with the real stuff: options, RSUs, vesting schedules, and dilution mechanics. Don't settle for the financial equivalent of a participation trophy when you should be getting a piece of the pie.

In this week's edition:

• Top delivery positions across product operations, program management, and implementation.

• Why everyone in tech is obsessing over Lenny Rachitsky's advice for modern PMs.

• A practical equity calculator that translates confusing offer paperwork into actual value.

• Lot’s more fun!

Let's dive in!

With Gratitude,

Phedra Arthur Iruke

Editor in Chief

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Featured Job Listings

🏆 Top Picks of the Week (Hand-Picked, High-Impact Roles)

Role: Vice President of Advancement

Company: Buzzards Bay Coalition | Leadership | Salary: 190k-220k + benefits

Location: New Bedford, Massachusetts
Why it’s great: Lead the charge in protecting one of New England’s most vital coastal ecosystems while shaping the fundraising and partnership strategy of a mission-driven organization. This VP role offers high visibility, impact, and a seat at the executive table.
Apply here: Email submission only. Job Link
Recruiter Contact: Paul Belsito, [email protected]

Role: Head of Program Management

Company: Thoughtful AI | Leadership | Salary: 200k-250k + employee stock options

Location: Remote or Austin, TX
Why it’s great: Lead program execution at Thoughtful AI, a company transforming healthcare by automating tedious admin work so providers can focus on patient care.

Apply here: [Direct Job Link]
Recruiter Contact: Anderson Clendenin | https://www.linkedin.com/in/andersonclendeninn/

Role: Senior Director, Program Management

Company: GameTime | Leadership | Salary: 170k-200k + benefits

Location: Remote
Why it’s great: Shape the future of live event ticketing at GameTime, where speed, scale, and fan experience matter. This role offers the chance to lead high-growth programs that directly impact millions of users.

Apply here: [Direct Job Link]
Recruiter Contact: Jasmina Thielke | https://www.linkedin.com/in/jasminathielke/

Role: Director of Program Management

Company: Caranet Health | Leadership 

Location: San Antonio, TX
Why it’s great: Lead transformative healthcare initiatives at Carenet Health, where your work directly enhances how millions of patients access care. This role offers executive-level impact in a mission-driven, fast-paced environment focused on innovation and outcomes.

Apply here: [Direct Job Link]
Recruiter Contact: Danann Smith | https://www.linkedin.com/in/danannsmith/

Role: Director of AI Strategy and Operations

Company: Prenuvo | Leadership | Salary 220k-330k

Location: Remote
Why it’s great: At a time when healthcare isn’t holistic in America, this company allows you to do a full body MRI scan to provide peace of mind. Shape the AI strategy at Prenuvo, a healthtech pioneer trying to catch disease early and make preventive care accessible to all.

Apply here: [Direct Job Link]
Recruiter Contact: Casey White | https://www.linkedin.com/in/casey-white-0a3a329a/

📌 More Hiring Now

Visionary Voices 

📝 Weekly Spotlight: Lenny Rachitsky - Product Wisdom for TPMs

Lenny Rachitsky's journey from software engineer to product oracle wasn't exactly linear. After co-founding Localmind (acquired by Airbnb in 2012), he spent seven years as a product lead at Airbnb during its hypergrowth phase. But it was his post-Airbnb pivot that cemented his status as the product world's most trusted voice.

In 2019, Lenny launched what became the gold standard resource for product professionals—a newsletter that's now 500k+ subscribers strong. His straight-shooting podcast followed, featuring no-nonsense conversations with leaders from Shopify, Stripe, and every other company you've bookmarked job listings from.

For TPM leaders specifically, Lenny's work offers several actionable frameworks worth stealing:

His "Ruthless Prioritization" methodology cuts through the chaos that plagues technical programs. Unlike traditional frameworks, Lenny advocates for what he calls "consequential prioritization"—focusing not just on impact and effort, but on the downstream consequences of what you choose not to build. When orchestrating cross-functional technical programs, this approach prevents the domino effect of abandoned dependencies.

On the people side, Lenny's research on high-performing teams reveals that technical program success hinges on what he calls "intellectual trust"—the belief that teammates will make good decisions without excessive oversight. His interviews with leaders at Figma and Notion highlight how this trust creates the psychological safety necessary for technical risk-taking.

What separates Lenny from generic thought leaders is his obsession with implementation details. His deep dives on goal-setting frameworks (particularly his adaptation of OKRs for technical programs) offer practical guidance for connecting strategic vision to daily execution.

For TPM leaders drowning in stakeholder management, Lenny's "influence without authority" playbook provides concrete communication patterns that maintain momentum across organizational boundaries.

The throughline in all his work? A pragmatic acknowledgment that product and program leadership is mostly about navigating complexity and contradiction—balancing long-term vision with short-term wins, technical excellence with time-to-market, and individual contributor growth with program outcomes.

Ready to transform your technical program leadership? Dive into Lenny's ecosystem:

👉 Subscribe to Lenny's Newsletter for weekly frameworks and tactics that outperform most MBA programs: lennysnewsletter.com/subscribe.

👉 Listen to Lenny's Podcast episodes with Shreyas Doshi (lennyspodcast.com/shreyas-doshi-on-tactical-frameworks-for-product-leaders) and Cristina Cordova (lennyspodcast.com/cristina-cordova-stripe-notion) for TPM-specific gold.

👉 Grab his "100 PM Lessons" course for battle-tested templates you can implement tomorrow: lennyrachitsky.com/courses.

Don't just manage programs—architect outcomes. Start with Lenny's masterclass at lennysnewsletter.com and turn your biggest program challenges into your competitive advantage.

📚 Equity 101 for Job Seekers

Because "you'll get 0.05%" isn't helpful unless you know what that means

So they've offered you equity along with your job offer. Great news—potentially. But let's be real: most candidates nod along when the recruiter explains their equity package, while secretly wondering what the hell it all means.

Here's what you actually need to know.

The Two Main Players: Options vs. RSUs

Stock options aren't actual shares—they're the right to buy shares at today's price (the "strike price") even after the company grows more valuable. The math is simple: if your strike price is $5 and the company eventually sells for $25 per share, you pocket the $20 difference per share. But if the company never increases in value? Those options might as well be Monopoly money.

RSUs (Restricted Stock Units) are actual shares the company promises to give you—no purchasing required. They're most common at later-stage companies and public companies. The catch? You'll pay income tax on their value when they vest, whether you can sell them or not.

Both typically vest over four years, often with a one-year cliff (meaning you get nothing if you leave before your first anniversary). The remainder usually vests monthly or quarterly thereafter.

Decoding Your Offer

When evaluating equity, these are the questions that actually matter:

What percentage of the company am I getting? Not how many shares—the percentage. 50,000 shares sounds impressive until you learn there are 500 million shares outstanding.

What's the current valuation? This tells you what your equity is theoretically worth today. A pre-money valuation of $10M means each 1% is worth $100K on paper.

What's the liquidation waterfall? Investors typically get their money back first through preferred shares. Your common shares might be worth less than you think in an exit that's not a home run.

What's the exercise window? If you leave the company, how long do you have to purchase vested options before they evaporate? The standard 90 days can force tough decisions.

What dilution should I expect? Each funding round will dilute your ownership. That's normal, but understanding the company's fundraising plans helps set expectations.

The hard truth is that most startup equity ends up worthless. But for the right company at the right stage, equity can change your financial trajectory forever. Just make sure you're gambling with eyes wide open—and never accept a below-market salary based on equity promises without understanding exactly what you're getting.

When in doubt, ask the hiring manager or recruiter to explain in concrete dollar terms what your equity could be worth in different exit scenarios. The good ones will walk you through it without hesitation.

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