How to Hire a Product-Led Sales Leader – at Every Stage

October 3, 2023

The world of sales continues to evolve with the popularization of product-led growth (PLG). PLG is an end-user-focused growth model in which the product itself drives acquisition, activation and expansion. Giants like Slack, Zoom, and Notion have inspired a new generation of startups to consider PLG instead of traditional go-to-market (GTM) strategies such as top-down sales.

However, starting out with PLG as the primary GTM strategy poses new hiring challenges – particularly when a startup is running a top-down sales motion at the same time. PLG as a strategic model is still relatively new, so finding sales leaders who can lead a product-led revenue organization can be a challenging hiring goal.

A nuanced understanding of the end-user lifecycle, hands-on experience with various pricing and conversion models, and an aptitude to make data-driven decisions are qualities that define a great product-led sales leader. The rarity of these unique skill sets in addition to the conventional challenges in finding a great sales leader makes it nearly an impossible task.

In a top-down sales organization, revenue growth is primarily driven by its sub-functions such as sales development, sales, sales engineering, and customer success. The sales leader has a complete span of control and requires much less cross-functional dependency to be successful.  By contrast, a product-led sales leader has a much broader function. They must collaborate with the product team to shape end-user experience, work with marketing to drive automated messaging and conversion, and organize all the data and insights to develop a much more intricate sales playbook.

The challenges of hiring a product-led sales leader differ across business stages, and so do the sales leader’s roles.

Early Stage

For PLG startups to be successful, there’s more often than not a product-oriented founder who is obsessively designing the user experience and acquisition funnel. Similar to founder-led sales in top-down sales motions, the best early stage startups tend to delay passing the torch until early signs of success whether that’s observed via prolific user sign-ups or engagement/usage metrics.

So rather than fueling growth with a traditional sales leader hire, we see PLG startups go for a demand gen marketer (to accelerate top of funnel) or a product manager with a very strong analytical background (to optimize conversion and activation funnel). In some verticals such as open-source software, we’ve also seen the rise of Developer Evangelists and community-led growth strategies which effectively drive awareness and demand into the PLG funnel.

If the founder wants to supplement GTM experimentation with top-down sales, we would recommend that the founder allocate more time to selling and customer discovery calls instead of prematurely hiring for the role until there’s substantial validation that contract values are large enough to support a dedicated salesperson.

Scale-Up Stage

Since hitting peak sensationalism around PLG (spoiler alert: it’s really hard to pull off), we’ve arrived at a more balanced viewpoint in which PLG is merely a GTM tool that can often be applied successfully alongside traditional sales and marketing strategies. In fact, most software companies nowadays are doing some version of PLS (product-led sales) in which the sales team is leveraging product-driven GTM success to prioritize and run top-down sales motions on the most engaged and highest potential opportunities.

Even in Zoom’s prolific growth story leveraging PLG, they invested in building a top-down sales organization fairly early in their journey. In fact, Dave Berman was infamously hired in 2015 to build Zoom’s sales organization. That investment was instrumental in preparing Zoom for the pandemic-induced surge of customer demand. Larger customers expected a high-touch buying experience and self-service would have faltered on its own.

For startups that have early signs of PLS success, targeting sales leaders with previous lived experiences scaling with a PLG startup is a tough but feasible search. With many trailblazing PLG startups that achieved massive scale and invested in top-down sales, it’s now possible to find many more early account executives, growth leaders, and front-line managers who are ready to export their knowledge.

Here are a few tactical best practices for making this hire:

  • What title should they have? Head of Revenue or Head of Growth are prudent interim leadership titles. There’s a high likelihood that a more senior executive will inevitably be hired above them as a startup scales. A title such as VP or CRO could set the wrong expectations with the candidate and the rest of the GTM organization.
  • What level to hire for? For most startups in the scale-up stages, it is less risky to hire someone who was in the weeds and saw the playbook built rather than hiring an executive who was too far removed from the details. Ultimately they have to build a playbook from scratch and know what “great” looks like up close.
  • How to assess candidates? A simple way to assess candidates is to give them some anonymized product and CRM data, and ask them to describe in detail how they would build the playbook from scratch. Great candidates can outline a very detailed plan based on their lived experiences.

Growth Stage

In the growth stage, there are strong incentives to consolidate all the GTM teams under a single commercial leader. Whether that’s a Chief Revenue Officer (CRO) or the increasingly popular Chief Commercial/Customer Officer (CCO), having a single executive leader responsible for revenue growth and customer satisfaction aligns competing priorities towards a single unified goal: driving growth.

The challenge in this stage is that every organization is unique. Industry/product type, revenue split (between PLG, enterprise sales, channel, etc.), and the capabilities of its existing business unit leaders can define the archetype of PLG sales leader most appropriate for the organization. While it’s easier to anoint a C-level executive by promoting from within, most high growth startups don’t have internal leaders with the necessary experience who are ready to lead the charge. The good news is that the executive talent pool is quickly growing as more startups and incumbents incorporate PLG into their core GTM strategy.

Examining the backgrounds of some of the top PLG companies in OV’s PLG Index, it’s clear there’s not a single way to go about leadership design. However, revenue executives at PLG companies draw upon three sets of competencies: sales, growth and product.

Looking at common patterns of prior experience and achievements, we see leaders that have:

  • Rigorous analytical and strategy experience from management consulting or financial services firms
  • Strong operational and analytical pedigree, observed from work experience and/or education
  • Led sales or customer success at SaaS companies with product-driven experiences
  • Led teams that sold or served SMB, mid-market and enterprise
  • Built foundational playbooks in growth marketing or had experience with product management (especially product analytics and monetization)

The goal of the search is not to find an executive with all of these lived experiences (nearly impossible), but to find the right blend of strengths to compliment the unique needs of the organization. For example, if a company already has a strong PLG product leader, then they should focus on finding an executive with more of a traditional sales leadership background. The jobs-to-be done in an organization is fungible and there are many ways to design around experience gaps.

In summary, while product-led sales leaders are still a relatively new breed of leadership hires, startups do have great options so long as they are intentional about stage-appropriate organizational design.

How to Hire a Product-Led Sales Leader – at Every Stage_OpenView Blog

Jordan Wan

Founder & CEO

Jordan Wan is the Founder & CEO of CloserIQ (, a leading GTM-focused executive search and recruiting firm that has scaled 900+ startups from Seed to IPO including companies like Riskified, Adyen, Algolia, Justworks, Asana, and Oscar Insurance. Since 2014, CloserIQ has partnered with leading venture capital firms to offer a unique, integrated approach to scaling GTM teams. We help early stage startups recruit founding account executives and then help them scale rapidly with a deliberate methodology in hiring stage-appropriate GTM executives.