Janine O'Neill, co-founder of ElevenX Talent, has over 20 years of experience helping startups find and hire top executive talent. With an MBA from UC Berkeley and certification as an Integral Coach, Janine leverages her background in recruiting, leadership development, and advising to partner with early-stage and growth-stage companies to build out their go-to-market teams.

In this episode, Janine shares her learnings on navigating the challenges of hiring the right executives at the right time. She breaks down the evolving dynamics between sales, marketing, and customer success, and reveals the red flags that make candidates wary of joining certain startups.

Janine's wisdom and tactical advice are a must-listen for any founder looking to avoid costly missteps and put their startup on the track to success. Her unique perspective, honed through years of working with top-tier startups and VCs, is both eye-opening and immediately actionable.

Catch the full episode with Janine here:

Here are my top 5 takeaways from our conversation:

[02:30] Hiring the right go-to-market executives at the right time

[27:51] Building trust in go-to-market hires' expertise

[29:29] Setting realistic expectations for ramp-up time

[36:11] Recognizing when a product is not ready for the enterprise market

[41:24] The importance of grit and self-awareness in founders

Let's dive into each of these key insights and explore how you can apply them to your own startup journey.

1. Hiring the Right Go-to-Market Executives at the Right Time

Janine emphasizes that the ideal first go-to-market hire depends on the unique situation of each startup.

"Every situation is different. I can imagine there are scenarios where a product marketer could be the first ideal go-to-market hire. One scenario would be if it's a category-creating product."

The decision to hire a product marketer, sales executive, or other go-to-market role first should be based on the specific needs of the startup, such as whether the product is creating a new category or entering an established market. Founders must carefully assess their startup's unique requirements and stage of development to determine the most critical go-to-market roles to fill first.

2. Building Trust in Go-to-Market Hires' Expertise

One of the primary reasons go-to-market executives leave startups is a lack of trust from the founders they report to.

"The number one reason people leave companies is because they're leaving people, not the company itself. For a leadership role in go-to-market, it's very often the feeling that their skill and knowledge is not trusted by the person they report to."

Founders must learn to trust the expertise and experience of the go-to-market leaders they hire. By providing autonomy and support, founders can create an environment where these executives feel valued and empowered to drive growth effectively. Building trust is essential for retaining top talent and fostering a collaborative, high-performing go-to-market team.

3. Setting Realistic Expectations for Ramp-Up Time

Janine highlights the importance of setting realistic expectations for the time it takes new go-to-market hires to ramp up and deliver results.

"For an enterprise sale, it could take nine months. For a regular SaaS, mid-market, or SMB sale, it could be three to six months. The idea is that results don't happen within a month of them joining. There's a lot of investment that you have to make in every person."

Founders should understand that building a successful go-to-market team takes time. Expecting immediate results can lead to frustration and high turnover. By providing adequate onboarding, training, and support, founders can help their new hires ramp up effectively and lay the foundation for long-term success.

4. Recognizing When a Product is Not Ready for the Enterprise Market

Many startups struggle when trying to move upmarket from SMB to mid-market or enterprise sales without adequately preparing their product.

"SMBs want to go upmarket and sell to mid-market or enterprise customers, but they haven't recognized how different their product has to be to sell to that market. It happens over and over. It's like pushing a rock up a hill, and in the middle of the hill, the rock starts rolling back down. That's a product that's not ready for enterprise."

Founders must honestly assess their product's readiness for the enterprise market. Attempting to sell to enterprise customers without the necessary features, scalability, or support can lead to frustration for both the sales team and the customers. Founders should work closely with their product and engineering teams to ensure the product is robust enough to meet the demands of larger customers before pursuing enterprise sales aggressively.

5. The Importance of Grit and Self-Awareness in Founders

Janine emphasizes that while grit is essential for founders to persist through challenges, self-awareness is also a valuable trait when building a go-to-market team.

"I would say that self-awareness is a huge bonus among the founder population, but what's most beneficial to a founder is the grit to persist in front of naysayers and keep forcing their company forward, even under a lot of headwinds."

Grit allows founders to push through obstacles and maintain momentum, even when faced with skepticism or adversity. However, self-awareness enables founders to recognize their own strengths and weaknesses, adapt to feedback, and make better decisions when building and leading their teams. A combination of grit and self-awareness can help founders create a resilient, adaptable, and successful go-to-market team.

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