How to Close a VP of Engineering Candidate Who Has Offers from Stripe and Datadog
Samira Okafor calls you at 4:37pm on a Thursday. She is measured, professional, and transparent: "I have offers from Stripe and Datadog as well." Your heart rate ticks up. Four months of searching. Unanimous first choice from the CEO and CTO. And now she is comparing your Series B startup — $40M raised, $340K base plus 0.3% equity — against Stripe at $385K and Datadog at $370K with a strong RSU package. The math is not in your favor. It never is when you are a startup competing against public companies with liquid stock. But Samira did not call to reject you. She called to talk. That means the door is open — barely, quietly, but open. What you say in the next 30 minutes either closes a hire that transforms your engineering org or sends you back to square one with a search that has already consumed 120 days.
Why This Conversation Goes Wrong
You try to compete on cash compensation. Matching Stripe on base salary would break your comp framework and set a precedent that haunts every future executive hire. You cannot win an auction against publicly traded companies. Trying tells Samira you do not understand your own value proposition.
You disparage the competing offers. "Stripe is a great company, but..." Any sentence that follows "but" is heard as jealousy. Samira has been in leadership long enough to recognize insecurity. Respect for the competition demonstrates confidence in your own position.
You create artificial urgency. "Our offer expires in 48 hours" feels like pressure, not enthusiasm. Samira explicitly said she does not make career decisions under pressure. Artificial deadlines signal that you are afraid of what happens when she has time to think — which is the opposite of confidence.
You fail to hear what she is not saying. Samira will ask about "the leadership team" and "what the exec team looks like." These are not small-talk questions. She is a woman evaluating whether she will be the only woman in the executive suite. She will never say this directly. If you answer with org charts instead of culture, you miss the question she actually asked.
The Decision Architecture
When a candidate has competing offers, the conversation is not about selling your opportunity. It is about helping them build a decision framework that naturally favors what your company uniquely offers. The Decision Architecture method shifts Samira from comparing spreadsheet columns to evaluating career trajectories.
Validate the competition genuinely
"Stripe and Datadog are exceptional companies. If I were in your position, I would take those offers seriously too." This disarms the adversarial framing instantly. Samira expected you to pitch against them. Instead, you earned her trust by acknowledging reality.
Shift from compensation to decision criteria
"Setting the numbers aside for a moment — when you imagine yourself 18 months from now, what does the best version of that look like?" You are moving the conversation from a spreadsheet comparison to a career vision conversation. The startup wins on vision, not on comp.
Listen for the unspoken concern
When Samira asks about the leadership team or executive composition, probe deeper: "What matters to you about the people you would be working alongside?" If she hints at representation, respond with specifics: who is on the team, what the company has invested in, and what the culture actually looks like at the leadership level. Generic platitudes about "valuing diversity" will cost you the candidate.
Frame equity as a career bet, not a gamble
"At Stripe, you would be an excellent VP in a machine that runs without you. Here, you would be the person who built the machine. That 0.3% represents a fundamentally different kind of career outcome." Do not paper over the risk. Acknowledge it, then reframe what the risk buys.
Help her sell it at home
If Samira trusts you enough to mention her spouse's concerns about equity versus cash, do not dismiss it. "I understand — equity is a bet, and that bet affects your family. Would it help to connect your spouse with our CFO for a transparent conversation about our financials and runway?" You are solving the kitchen-table conversation, not just the boardroom one.
The moment that changes everything
The highest bidder almost never wins VP-level candidates.
Samira is leaning toward your startup. She has not told you that, and she will not until you earn it. The reason is not the equity upside or the title. It is the scope. At Stripe, she would inherit an engineering organization that was built by someone else and optimized over years. Her fingerprints would be incremental. At your company, she would build the entire engineering function from 40 to 200 people. That is the kind of career-defining work that gets her invited to keynote conferences five years from now. But Samira cannot justify a $45K base salary gap and illiquid equity to her spouse by saying "I want to build something." She needs you to help her construct the rational case for an emotional decision. When you frame the equity as a career multiplier, connect her to the CFO for a transparent runway conversation, and demonstrate that the executive team is one she would be proud to join — the spreadsheet comparison loses its power. Samira will not choose the highest number. She will choose the clearest story about who she becomes.
What to Say (and What Not To)
Instead of
"Our equity could be worth millions."
Try this
"At 0.3%, you would own a meaningful piece of what you build. Let me connect you with our CFO so you can evaluate the financials directly."
Instead of
"We need to know by Friday."
Try this
"Take the time you need to make this right for yourself and your family. I would rather you choose us with full conviction than feel rushed."
Instead of
"We value diversity — it's really important to us."
Try this
"Our Head of Product is Maya Chen and our VP of Customer Success is Priya Sharma. Here is what they told me about why they chose this company."
Instead of
"Stripe is a big company — you'd be a number there."
Try this
"Stripe is an incredible company. The question is whether you want to optimize an existing machine or build one from scratch. Both are valid — but they are different careers."
The Bigger Picture
Hired.com analysis of 98,000 offers found that candidates who accepted startup offers over competing public-company offers cited "scope of impact" as the primary factor 61% of the time — above compensation, title, and brand. Startups lose when they try to compete on comp. They win when they compete on career trajectory.
A Spencer Stuart study of executive hires found that VP and C-level candidates whose spouses or partners were included in the evaluation process — through office visits, CFO conversations, or relocation support — accepted offers at a rate 34% higher than candidates whose families were excluded from the process. The kitchen-table conversation is the real close.
Practice This Conversation
12 minutes · AI voice roleplay with Samira Okafor
Reading about this is step one. Practicing it changes everything. Sonitura lets you rehearse this exact conversation with Samira Okafor, a realistic AI engineering director considering three vp of engineering offers who reacts to your words in real time. It takes 12 minutes. When Samira calls with competing offers, you will not panic. You will already know exactly how to shift the conversation.
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