Hiring the right go-to-market (GTM) leader is one of the biggest challenges startup Founders face as their business grows. In the early days, Founders often juggle sales, marketing, and customer success themselves, adjusting strategies on the fly. But at some point, wearing too many hats slows progress, and specialized leadership becomes essential to scale effectively.
The decision to hire a GTM leader, however, raises many questions: When is the right time? What should you prioritize in a candidate? How do you balance immediate needs with long-term growth? These decisions can feel overwhelming, especially if you’re hiring for roles outside your expertise—like a technical Founder bringing on a sales leader for the first time.
To tackle these challenges, Le Thorkelson, VP of Talent Network at Redpoint Ventures, shared practical insights on a recent podcast. Drawing from years of experience working with startup Founders, Le offers advice on recognizing when to hire, avoiding common mistakes, and ensuring your new leader succeeds.
This guide builds on his expertise, giving you actionable steps to find the right leader who fits your company’s needs and drives sustainable growth. Let’s dive into the key takeaways from his conversation and how you can apply them to your hiring process.
A Comprehensive Guide to Hiring Go-to-Market Leaders for Startups
What is a Go-to-Market Leader?
Go-to-market (GTM) leaders are the architects of growth for startups, ensuring a seamless connection between a product and its customers. As Le Thorkelson explains, these leaders design systems that align sales, marketing, and customer success into a unified strategy.
Their focus isn’t just on managing teams—they create scalable processes like repeatable sales strategies and structured onboarding to ensure the business grows efficiently. They help sales close the right deals, attract high-quality leads through marketing, and build loyalty with customer success. GTM leaders transform ad-hoc efforts into a structured, repeatable approach, preparing startups for consistent results and sustainable growth.
Why Founders Need GTM Leaders
In the early stages, Founders typically handle everything—from sales to customer relationships to strategy. While this hands-on approach works for a time, it eventually becomes a bottleneck. Scaling requires focus, and Founders managing too many roles can’t dedicate themselves to innovation and growth.
GTM leaders step in to take the burden off Founders by introducing structure and scalable systems. They shift sales from personal, relationship-driven efforts to strategies that expand reach and deliver consistent results. As Le Thorkelson points out, the right GTM leader doesn’t just boost revenue—they align teams, build sustainable systems, and allow Founders to focus on the big picture. By stepping in at the right time, they help startups transition from survival mode to strategic growth.
When Should Founders Hire a Go-to-Market Leader?
According to Le Thorkelson, the decision to hire a go-to-market (GTM) leader often becomes clear when Founders find themselves stretched too thin. If managing sales, customer interactions, and product development consumes your time and energy, it’s a sign that you’ve reached a ceiling. Burnout, inconsistent sales processes, or missed growth opportunities are red flags that the business needs specialized leadership to keep scaling.
The timing of this hire is critical. Le emphasizes that hiring early, before these challenges escalate, allows you to plan effectively and avoid rushed, reactive decisions. Since finding the right GTM leader can take months, waiting too long often results in settling for the wrong candidate or stalling growth.
A proactive approach involves forecasting when your sales and customer efforts will need more structure and planning your hire accordingly. If your business is struggling to maintain momentum, streamline sales, or balance leadership priorities, it’s likely time to bring in a GTM leader to support your next stage of growth.
Best Practices for Hiring Go-to-Market Leaders
Le Thorkelson emphasizes that hiring a go-to-market (GTM) leader is a pivotal moment for any Founder, requiring careful planning and clear strategies. Based on his insights, here are five key practices to guide you through the process:
Hiring for Present and Future Needs
A GTM leader must solve today’s challenges while preparing your business for tomorrow’s growth. They need to deliver immediate results while having the potential to scale with your company. As Le pointed out, hiring someone who can grow into a larger role is ideal—but only if they’re capable of meeting current needs first. A mismatch here can derail progress early.
Overcoming Founder Bias in Hiring
Founders often struggle when hiring for roles outside their comfort zone. For instance, technical Founders may feel confident hiring engineers but hesitate when evaluating sales or marketing professionals. This bias can lead to poor decisions or delays. Involving experienced advisors, mentors, or recruiters provides fresh perspectives and helps ensure you’re evaluating candidates objectively.
Defining the Role Clearly
Ambiguity in a job description creates confusion and sets both the candidate and your company up for frustration. Clearly outline the GTM leader’s responsibilities and ensure they align with your company’s goals. Avoid hybrid roles that combine unrelated tasks, like expecting a VP of Sales to also manage customer support. Clarity ensures focus, effectiveness, and alignment from day one.
Leveraging Your Personal Network
Your network is one of your most valuable hiring tools. As Le noted, individuals you’ve worked with in the past could become future hires, advisors, or board members. Use a simple CRM or system to track promising contacts and maintain relationships over time. This approach builds a steady pipeline of high-quality candidates and can save you time when it’s time to hire.
Preparing for the Hiring Process
Before starting your search, educate yourself on what makes a great GTM leader. Speak with leaders who’ve held similar roles, consult your board, or connect with Founders who’ve faced the same challenges. Le recommends working with executive recruiters to gain market insights and understand what candidates are looking for. Time spent preparing upfront saves time and frustration later.
These strategies provide the foundation for hiring a GTM leader who not only meets your company’s immediate needs but also helps drive its long-term growth. Once you’ve secured the right hire, the next step is setting them up for success. Let’s dive into that next.
Evaluating and Selecting the Right Candidate
Le Thorkelson emphasizes that finding the right go-to-market (GTM) leader is about identifying someone who can drive growth and align with your company’s culture. Follow these five steps to make the right choice:
Step 1: Look for a Business-Wide Perspective
A great GTM leader isn’t limited to their department—they think about the entire business. They ask insightful questions about the product, customers, and goals, demonstrating a long-term mindset.
Step 2: Focus on Customer-Centric Leadership
Prioritize candidates who build lasting relationships with customers rather than chasing short-term wins. Their ability to create value for customers aligns directly with your company’s growth.
Step 3: Ensure Cultural Alignment
A successful GTM leader doesn’t just deliver results—they integrate seamlessly with your team and embody your company’s values. Their ability to build trust and foster collaboration is critical for long-term success.
Step 4: Assess Depth Over Charisma
Charisma alone won’t cut it. Exceptional leaders demonstrate strategic thinking, a strong grasp of your product and market, and the ability to execute. Look for candidates who prioritize talent recruitment and align their efforts with your long-term vision.
Step 5: Verify Through Results and References
Don’t rely on impressions alone—dig into their past achievements. Look for evidence of their ability to design scalable systems, attract top-tier talent, and consistently deliver results. References can validate their skills and leadership style.
Five Common Pitfalls to Avoid When Hiring a GTM Leader
Le Thorkelson highlights several mistakes Founders often make when hiring go-to-market (GTM) leaders. Avoiding these pitfalls can save you time, money, and frustration:
How to Avoid These Mistakes
- Prepare thoroughly before starting the hiring process.
- Clearly define the role and align expectations.
- Seek input from trusted advisors to ensure well-rounded decisions.
By avoiding these pitfalls, you’ll make confident, informed hiring choices and secure a GTM leader who can drive long-term growth.
How To Support Go-to-Market Leaders Post-Hire
Hiring a go-to-market (GTM) leader is just the start. To help them succeed, Founders need to provide clarity, alignment, and consistent support from day one. Here’s how to set them up for impact:
- Set Clear Goals and Expectations
Define their role and how it ties into your company’s objectives. Clearly outline short-term and long-term success metrics so they know where to focus. Clarity from the start ensures priorities are aligned and actionable. - Ensure Team Alignment
Help them integrate into your team and culture by fostering collaboration across departments like sales, marketing, and product. Open communication prevents silos and ensures everyone is working toward the same goals. - Track Early Results
Monitor their early contributions to gauge impact. Le Thorkelson highlights key indicators like improved customer interactions, faster sales cycles, and quality team hires. By the next board meeting, their results should be clear. - Support Without Micromanaging
Trust their expertise while staying available to remove roadblocks or address challenges. Give them the freedom to execute their strategies while ensuring alignment with your vision. - Establish Feedback Loops
Schedule regular check-ins to review progress, address gaps, and adjust strategies as needed. These touchpoints keep everyone aligned, maintain momentum, and encourage continuous improvement.
By providing clear expectations, trust, and ongoing support, you’ll empower your GTM leader to make a meaningful impact on your business growth.
How to Overcome Common Challenges in Go-to-Market Roles
Le Thorkelson emphasizes that while hiring a go-to-market (GTM) leader is critical, ensuring their success requires overcoming common challenges. Here’s how to address key obstacles:
1. Balancing Multiple Hats in Early-Stage Startups
In the early days, GTM leaders may take on a mix of responsibilities, such as sales, customer success, or marketing. While flexibility is helpful, overloading them with unrelated tasks can dilute their focus. Keep their primary role clear and achievable to maximize their impact.
2. Defining Success Early
Founders often fail to set clear metrics to measure a GTM leader’s success. As Le noted, sales roles require immediate impact. Early indicators include shorter sales cycles, stronger customer interactions, and high-quality hires. Establish measurable goals from the start to avoid ambiguity.
3. Dealing with Ambiguous Roles
Hybrid or poorly defined roles often lead to confusion and inefficiency. For example, asking a VP of Sales to manage both revenue growth and customer support can result in underperformance. Instead, define roles clearly while allowing manageable overlap where necessary.
4. Trusting Their Expertise
Founders can struggle to let go and trust their GTM leader’s judgment, especially in unfamiliar areas like sales or marketing. Micromanaging limits their ability to deliver results. Provide support where needed, but give them the freedom to execute their strategies.
5. Adapting as the Business Scales
The role of a GTM leader will evolve as your business grows. Be open to adjusting their responsibilities or adding resources to support them. As Le pointed out, great leaders grow with the company and often contribute to multiple areas over time.
By clearly defining roles, setting early success metrics, and allowing your GTM leader room to lead, you’ll overcome challenges and create a solid foundation for long-term growth.
Conclusion: Setting Your Business Up for Success
Hiring the right go-to-market (GTM) leader is a transformative step for any growing startup. As Le Thorkelson shared, this role goes beyond filling a gap—it’s about bringing in someone who can align teams, drive scalable processes, and set the foundation for long-term growth.
By understanding when to hire, avoiding common pitfalls, and following best practices for selecting and supporting your GTM leader, you can ensure they deliver immediate results while growing with your business. Clear expectations, a well-defined role, and ongoing trust are key to empowering them to succeed.
This process isn’t just about adding a leader to your team; it’s about creating a structure that allows your company to thrive. With the right GTM leader in place, you’ll have the freedom to focus on your vision, innovate, and scale confidently.
Now it’s time to take these insights and apply them to your hiring journey. The right GTM leader isn’t just a hire—they’re a partner in building your company’s future.
