Executive
Compensation
Guide
Introduction
Executive Hiring Is Getting Smarter—And So Should Compensation
As startups navigate tighter budgets, shifting buyer behavior, and a surge in AI-powered competition, one thing is clear: hiring your first department head isn’t just about finding talent—it’s about making the right strategic bet.
The role of a first-time executive has changed. Founders are no longer looking for functional leaders who can “figure it out.” They want partners—people who can build departments from scratch, drive measurable growth, and align with long-term business goals.
This guide breaks down what’s happening in the market right now. Inside, you’ll find:
- 2025’s biggest trends in executive hiring and compensation
- A breakdown of what early-stage companies should look for in their first Heads of Sales, Marketing, and Customer Success
- A “choose your own adventure” section to tailor your executive search based on who your team sells into—technical buyers vs. traditional industries
- Compensation negotiation strategies tailored to first-time executives
There Are 4 Parts to the Executive Compensation Guide
2025 Trends
1
For early-stage startups hiring their first Heads of Sales, compensation structures continue to prioritize equity over high base salaries. With cash constraints still prevalent in Series A and B companies, leaders willing to bet on the company's long-term success can negotiate meaningful ownership stakes. However, candidates should ensure clear equity terms, including vesting schedules, tax structures, and exit scenarios.
For more information, visit Mary Russel's Stock Option Counsel, P.C. – One of our partners
Equity Remains King for First-Time Sales Leaders
2
Hiring a first Head of Sales isn’t just about bringing in a top performer—it’s about finding someone who can build a repeatable sales process. More companies are emphasizing candidates who have successfully scaled from $0 to $10M ARR, focusing on their ability to hire and train a team, define ICPs, and optimize sales motion. Expect in-depth interview processes that include GTM strategy presentations and backchannel reference checks.
Head of Sales
The First Head of Sales Must Be a Builder, Not Just a Closer
Backchannelling is More Common Than Ever
Companies are investing more in pre-hire due diligence, especially for first-time executives. With the risks associated with hiring an unproven leader, VCs and founders are leveraging their networks to discreetly verify candidates’ past performance. While backchanneling has become a common practice, it shouldn’t be the sole deciding factor in a hiring decision. Executives should proactively manage their professional reputation and be prepared for informal reference checks that go beyond their listed references.
3
Customer retention and expansion are driving revenue strategies in 2025, placing a premium on Heads of Customer Success who can own renewals and expansion. Companies are looking for leaders with experience implementing scalable playbooks, leading post-sale revenue teams, and collaborating closely with product and sales. A strong product feedback loop is also a must—leaders are expected to capture and relay insights from customer interactions to help shape the product roadmap. Compensation models increasingly include upside potential tied to Net Revenue Retention (NRR).
The Rise of Customer-Led Growth Increases Demand for Strategic CS Leaders
Strategic CS
4
Marketing leaders in 2025 must prove they can directly impact pipeline and revenue. Founders and boards are scrutinizing marketing hires, favouring those with strong performance marketing, ABM, and sales alignment experience. Compensation structures increasingly tie incentives to pipeline creation and influenced revenue. Account-based marketing is especially critical for companies facing heavy competition or operating in emerging categories, where differentiation and targeted outreach can make or break growth.
Heads of Marketing Need to Be Demand Drivers, Not Just Brand Builders
Head of Marketing
5
Executives vying for their first leadership role must navigate a rigorous interview process. Companies want to see not just past achievements but also a clear vision for scaling the function. Successful candidates should come prepared with data-driven playbooks, examples of cross-functional leadership, and a deep understanding of financial metrics.
6
Interviewing for First-Time Executive Roles Requires More Strategy Than Ever
In smaller startups that lack the resources for a full executive team, it’s becoming increasingly common for a single leader to oversee both sales and marketing. This VP-level role requires expertise in both disciplines, as well as the ability to align GTM strategies across functions. AI, GEO, SEO, and automation are streamlining sales and marketing efforts, enabling leaner teams to do more with less. For companies without a Chief Revenue Officer (CRO), the Head of Sales & Marketing is expected to take on broader responsibilities, driving both pipeline generation and revenue growth. AI is reducing manual workload by automating lead qualification, content personalization, and sales forecasting, allowing leaders to focus on strategy rather than execution. Predictive analytics help unify sales and marketing efforts by identifying high-intent prospects and optimizing outreach timing. With AI improving efficiency across the funnel, a single leader can now manage both functions without compromising growth.
7
The Rise of Crossover Execs
Hiring decisions for GTM leaders are increasingly shaped by who your company sells to, not just what you're selling. It's no longer enough to hire based on strong resumes or past company names. The most effective leaders are those who understand how to engage, sell to, and support the specific buyers your business depends on.
Sales, marketing, and customer success executives need different skill sets depending on whether they're operating in a technical, fast-evolving environment—or navigating long, complex sales cycles in traditional industries.
These differences aren’t superficial. They determine how quickly your GTM leaders can ramp, how well they’ll align with your buyer’s expectations, and how effectively they’ll drive growth.
Head of Sales
A Head of Sales who excels with technical buyers may fall short when selling into compliance-heavy environments.
Head of CS
A Customer Success leader who shines in usage-driven SaaS may struggle with renewal cycles tied to policy, regulation, or long-term adoption.
Head of Marketing
A marketer who performs in enterprise software may miss the mark when repositioning outdated workflows in risk-averse verticals.
8
Buyer-Aligned Hiring Is Reshaping Executive Searches
Who Are You Selling To? Choose Your Own Adventure
- Before hiring your next executive, ask: Who are we selling to—and what kind of leader knows how to win their trust?
- The next section breaks this down into two distinct paths based on your buyer profile: Technical AI Buyers vs. Buyers in Traditional Industries
- Each path outlines what to look for in a Head of Sales and Head of Customer Success based on who they’ll be selling to and supporting.
What to Do Next
Whether you're hiring for Sales or Customer Success, the profile of your executive should reflect the type of buyer your company is targeting. In 2025, that means aligning your leadership with one of two major go-to-market realities:
Disruptive Industry Innovators
Companies modernizing traditional industries—legal, healthcare, manufacturing, government, and more. These buyers may be non-technical, risk-averse, and slower to adopt new tools, but the opportunity for category creation is significant.
Technical AI Companies
Companies building advanced software or infrastructure products, often selling into highly technical teams (CTOs, CIOs, CPOs). These buyers expect depth, detail, and diligence.
Head of Sales: What to Look For
Complex sales experience
The sales cycles are long and technical. Your ideal hire has run multi-threaded enterprise deals, managed lengthy security reviews, and understands how to sell to multiple stakeholders—often including engineers, procurement, and compliance teams.
Credibility with technical audiences
While they don’t need to be technical themselves, your Head of Sales must be able to lead discovery and earn respect in the room. They should understand enough to explain how the product works and why it matters.
Structured process-building
The best candidates will bring rigor. They’ve built outbound engines, defined qualification criteria like MEDDPICC, and held teams accountable to pipeline and forecast discipline
Cross-functional operator
Expect them to work closely with Product, Engineering, and Marketing to tailor messaging and iterate fast.
Experience with hybrid GTM motions
Many AI companies start with a product-led approach, then layer on sales. A good sales leader knows how to complement PLG without disrupting it.
Path 1
Technical AI Companies
You’re building advanced AI products for technical buyers—CTOs, CIOs, CPOs, and their teams. These stakeholders expect rigor: technical depth, clear differentiation, and real-world results. Winning here means proving your product can integrate, scale, and deliver value from day one.
Head of Customer Success:
What to Look For
Technical onboarding programs
The right CS leader knows how to onboard users with different technical skill levels. They’ve likely built out implementation guides, run enablement sessions, and worked alongside solution architects.
Renewal predictability
In AI or infrastructure tools, usage doesn’t always equal value. Your CS leader should be great at setting up renewal processes that include qualitative health checks, not just usage metrics.
Support scalability
Expect them to define what should be self-serve vs. high-touch and how to scale without sacrificing client experience.
Customer education mindset
AI is evolving fast. Your CS leader should know how to keep customers informed about new features, capabilities, and use cases as your
product evolves.
Head of Sales: What to Look For
Evangelical storytelling
You need someone who can explain why now. They should know how to speak to pain points in simple language and frame your product as the
inevitable future.
Vertical GTM experience
The best candidates have sold into these sectors before. They understand how purchasing decisions are made, who the gatekeepers are, and how to
adjust messaging for each.
Flexibility and grit
Traditional industries often require more patience and creative problem-solving. Your Head of Sales should be used to navigating RFPs, pilots, and internal blockers.
Hands-on, founder-like energy
In early-stage companies, they’ll likely close deals
themselves while building the motion. They should thrive in ambiguity and work well across Product and CS.
Head of Customer Success:
What to Look For
Change management skills
This isn't just about adoption—it’s about behavior change. Your CS hire needs to understand how to guide customers through process shifts,
stakeholder buy-in, and cultural resistance.
Customization and consultative approach
Expect clients to ask for custom workflows, integrations, or hands-on support. A good CS leader here acts more like a trusted advisor than a ticket resolver.
Stakeholder orchestration
Traditional buyers often have multiple internal
stakeholders—operations, compliance, finance—who influence renewals and expansions. Your CS leader should be great at mapping and managing these relationships.
Patience with long-term payoff
Expansion cycles may take time, but once trust is built, these customers often have high LTV. Your CS hire should know how to play the long game.
Path 2
Disruptive Industry Innovators
You’re modernizing traditional industries like legal, healthcare, government, or logistics. Your buyers are smart, but they’re not early adopters. They may be wary of change, stuck in legacy workflows, or navigating regulatory constraints. Selling here requires education and trust.
Head of Marketing
Marketing leaders are unique—they don't just support Sales and CS. They shape the entire narrative of your company. Whether you're selling into technical or non-technical markets, your Head of Marketing needs to be a bridge between product, market, and growth.
What to Look For?
Full-funnel ownership
From top-of-funnel awareness to sales enablement and customer expansion, your marketing hire should know how to support each stage of the buyer journey.
Brand and positioning chops
Especially for category-defining companies, your marketer should have a strong POV on how to differentiate in a crowded or misunderstood market.
Revenue accountability
The best marketing leaders in 2025 are deeply tied to pipeline generation. They’ll come with dashboards, conversion targets, and a clear view of attribution.
Tactical and strategic range
Great early-stage marketers know when to run a quick LinkedIn ad test and when to lead a full rebrand. They’re just as comfortable in the weeds as they are in the boardroom.
Cross-functional savvy
Marketing needs to be joined at the hip with Sales, Product, and CS. Look for someone who’s driven roadmap alignment, coordinated product launches, and built integrated campaigns.
Early wins + scalable vision
Your hire should come in with a 30-60-90 day plan, but also be thinking two years ahead. They’ll lay the foundation for a team and engine that can scale with you.
How First-Time Executives Can Secure the Best Compensation Package
Landing an executive role is a major milestone, but securing the right compensation package is just as critical as getting the offer itself. First-time executives often face unique challenges in negotiations—especially at startups, where cash constraints and evolving company needs can make compensation highly variable. Founders may not have a set budget for the role and will expect candidates to advocate for themselves. The key is to balance cash, equity, and incentives in a way that aligns with both the company's growth trajectory and your long-term financial goals.
For first-time execs, it's not just about salary—it's about structuring a package that reflects your leadership impact and potential upside. Companies hiring their first function leaders may be flexible in how they structure offers, but candidates need to be prepared to negotiate terms that set them up for success.
Negotiation Strategies for First-Time Executives
Candidates
How to Maximize Your First Executive Offer?
Know Your Market Value
Cash vs. Equity: Know the Trade-Offs
Ask about valuation, dilution, and exit plans.
Tie Comp to Your Impact
Push for bonuses/equity tied to results.
Clarify the Role
Align on 6–12 month success metrics.
Perks Matter Too
Look beyond salary—think PTO, development budget, remote flexibility.
Leverage Optionality
Multiple offers = stronger negotiating position.
Get a Legal & Tax Review
Equity can be tricky—don’t go it alone.
Big Picture
You’re not just taking a job—you’re betting on a company. Bet wisely.
Hiring Managers
How to Win Over First-Time Execs?
Understand Their Market Value
Explain the Cash vs. Equity Mix
Be transparent on how equity works—vesting, dilution, exit.
Tie Comp to Company Outcomes
Align incentives with impact: revenue, retention, growth.
Set Clear Expectations
Define success. Make sure you both see the same path.
Go Beyond Salary
Use perks to close the deal: leadership coaching, flexibility, accelerated vesting.
Make It Personal
Take them to dinner or do a 3-hour whiteboard session.
Expect Negotiation
Smart execs will push back. Be ready—and open.
Think Long-Term
This isn’t just a hire—it’s a future partner in the business.
Compensation Breakdown
Compensation by Role
Chief Executive Officer (CEO)
Chief Operations Officer (COO)
Chief Financial Officer (CFO)
Chief Commercial Officer (CCO)
Chief People Officer (CPO)
Chief Marketing Officer (CMO)
Chief Product Officer (CPO)
Chief Revenue Officer (CRO)
Fractional
Advisors
VP of Sales
VP of Marketing
VP of People Ops
VP of Finance
VP of Product Management
VP of Customer Success
Director/Head of Marketing
Director of HR/Head of People
Director/Head of Product
Director/Head of Sales
Director/Head of CS
A Message From Betts
Founder and CEO
We hope you've found this guide helpful as you plan for the year ahead. With 2025 set to be an exciting year for the tech industry—driven by advancements in AI, enterprise strength, and a resurgence in mid-market hiring—now is the time to refine your compensation strategies and attract the best talent.
At Betts, we understand that talent is your most valuable asset, which is why we’ve created this guide to help you navigate the world of compensation. Built on data from thousands of successful placements and insights from leaders across the tech sector, this guide is designed to give you the tools to stay competitive and retain top performers.
We’re excited to continue partnering with you in 2025 and beyond as you drive growth and success. Here's to a fantastic year ahead!
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