How to Negotiate Startup Compensation When 100+ Candidates Apply Daily: Insights from Hilary Gardner

TL;DR: Don't negotiate in the dark. Know your worth, use multiple levers beyond base salary, and remember that recruiters are your allies, not adversaries.

In a market where startup job applications can hit 100+ within hours of posting, negotiating compensation feels like walking a tightrope. One wrong move and you're out. But according to Hilary Gardner, Director of Talent Acquisition at Inspiren, the key isn't avoiding negotiation—it's doing it strategically.

During our latest Ask a Recruiter live Q&A, Hilary shared hard-won insights from over a decade of recruiting across gaming, ad tech, music tech, fintech, and health tech. Her message was clear:

"You have to advocate for yourself. Companies are excited about you, but they don't have your best interests at heart. You do."

View the full session here:

The Foundation: Know Your Worth Before You Walk in the Room

"The biggest factor in negotiation is knowledge." This isn't just about knowing market rates—it's about understanding your complete value proposition.

Hilary's preparation checklist:

Your current compensation baseline
Years of experience and proven tenure (tricky post-COVID, but essential)
Your career arc and story
What you're bringing to the table vs. what you're taking

For research, Hilary recommends starting with Glassdoor for crowdsourced data, but warns: "It's Reddit, basically." More reliable sources include market data platforms like Pave, Wellfound's salary calculator, and job descriptions in states like New York, California, Colorado, and Massachusetts where compensation ranges are legally required.

The golden rule?

"Know your range. What's your bottom-out number? What do you need to pay bills, create savings, and build a six-month safety net?"

Timing is Everything: When and How to Start Compensation Conversations

"The first conversation with the recruiter at the beginning of the interview process should be where you start having salary conversations." Not with the CEO in the final round. Not even with the hiring manager. The recruiter is your compensation ally.

Legally, recruiters can only ask about your expectations for the next role—not your current salary. Use this to your advantage: "What are your current ranges? What have you seen on the market? Help me understand."

When you receive an offer, that's negotiation time. Hilary's framework for the conversation:

"I'm so excited about this opportunity. That [number], when we discussed in our conversation, I was hoping for [higher amount]. Explain to me why I'm not there. Help me understand how to get to [target number]."

The Current Market Reality: It's Brutal, But Rules Still Apply

When asked about negotiating in today's challenging market, Hilary was blunt: "This is the hardest market to be a candidate in. It is a buyer's market." With 100+ applications hitting roles on day one, candidates feel pressure to accept any offer.

But the same principles apply. You still need to know your worth and understand the complete package. "Base is not the only lever you have to pull. It's the total package, but you have to look at it from apples and oranges."

Her advice for candidates feeling desperate: Understand what matters most to you—not what matters to your finance-savvy partner looking over equity details. "What's important to you."

Beyond Base Salary: The Five Levers of Startup Compensation

Hilary outlined five negotiation levers candidates often overlook:

1. Title - Sometimes flexible, can impact future opportunities

2. Base salary - The guaranteed foundation

3. Bonus or sign-on - Immediate cash influx

4. Equity - Long-term upside potential

5. Benefits and perks - Often undervalued but meaningful

"Do you want a better title for 5K less? Do you want more equity for 10K of sign-on bonus and you're not getting your base salary?"

Companies have internal flexibility across these areas, even when base salary feels fixed.

The Corporate-to-Startup Reality Check

For candidates transitioning from larger companies, Hilary delivered tough love: "You are expensive. You're coming from an environment that rewards you for different things than a startup would."

The core issue? You don't have proven startup experience. Large organizations provide structure; startups require building that structure. "Are you going to walk in and be effective in 90 days if you're building something from scratch?"

Her recommendation:

"You might need to back up to go forward. That means taking a lateral move, potentially a pay cut to then grow in the right direction."

Think of it as a strategic investment: "Five years at a startup is like an MBA for a larger organization in certain roles."

Equity: The Black Box Demystified

When discussing equity negotiations, Hilary acknowledged the complexity: "Equity is very nuanced to each organization."

Key questions to ask:

What's the strike price?
What's the current valuation (the company's 409A, which determines option pricing)?
What does the cap table look like?
How many outstanding shares exist?

Her philosophy on equity:

"It's like a savings account. You're building something for the future. You're baking the cake and then you put the cherry on top—that's equity."

Red Flags and Reality Checks

Hilary shared a recent experience where she "lost a candidate because I overplayed my negotiation hand" over just $3K. Her takeaway: "That tells you that there's other reasons that they weren't gonna be a fit for the role."

When candidates get consistently shut down during compensation discussions, it might signal a poor recruiter or company culture. "You're still interviewing when you're negotiating."

The Two-Round Rule

Perhaps most importantly, Hilary established clear boundaries:

"You have two times back and forth with the company before you have to give your best and final answer. Anything more than that as a mid-level or junior person, even director level—two times max, one time is perfect."

Remember: This Isn't Forever

Throughout the session, Hilary emphasized a crucial mindset shift: "This is a starting number. You are not going to retire from this job at this number."

For candidates facing tough choices between lower compensation and growth opportunities:

"If it's five to 10K and it's really gonna be an opportunity for you to grow your career, challenge your status quo, learn something new—quantify that. What does that mean to you?"

Actionable Takeaways

1. Create a compensation spreadsheet tracking companies, ranges, and your bottom-line number before any conversations begin.

2. Start salary discussions with recruiters in your first conversation using: "Tell me about the range for this role"

3. Prepare your negotiation levers beyond base salary—title, sign-on bonus, equity, and benefits can bridge gaps when base salary is fixed.

4. Research thoroughly using Pave, Glassdoor, Wellfound's calculator, and job postings in transparency-required states.

5. Limit back-and-forth to two rounds maximum, and remember this is a starting point, not your forever number.

This article summarizes key points from Wellfound's 'Ask a Recruiter' live Q&A event featuring Hilary Gardner. To find out more candidate tips, check out other 'Ask a Recruiter' sessions on the YouTube playlist here.