As the past few years have demonstrated, it’s wise to expect the unexpected, especially when it comes to hiring. In particular, hiring for your sales team is critical in an uncertain economic outlook. Additionally, sales professionals looking for a new role should choose their next company wisely.

In this edition of CRO Confidential, Sam Blond, Partner at Founders Fund and former CRO at Brex, discusses the current SaaS sales landscape and tips for hiring in 2023 with guest Ben Braverman, Head of Flexport Fund and former Flexport CRO and CCO. 

Great Companies Attract Great Talent

Blond and Braverman have enjoyed successful careers as sales leaders in high-performing companies. However, as more workers have left their roles over the past few years and employee expectations shift, it’s important for both job applicants and hiring managers to understand what indicates a winning business.

Drawing from his experience, Braverman shares what attracted him to Flexport years ago when it was in its early stages. Flexport, a platform that focuses on supply chain management and logistics, was most recently valued at $8 billion and has proven its success since its founding in 2013. 

As part of the early team, Braverman describes how the founder Ryan Petersen was a big reason he chose Flexport: “Great founders are inherently compelling…when you meet them, you can feel in your bones that they are different kinds of human beings than most everyone else you’ve ever met.” This X-factor of the Flexport founder is part of what attracted Braverman to the business, but founder personality is important beyond how they make you feel –– it’s an indicator of how they will lead the company.

Besides the founder’s passion and ambition, two more reasons that Flexport was able to get excellent talent early were:

  • Founder-Market Fit: Is the founder uniquely qualified for their space? Are they equipped to solve the problem their business addresses? Do they have experience or aptitude relevant to the industry in which they operate?
  • Market Size: Examine the size of the market and its potential. What sort of opportunity is there for business? Is there any way to stand out or disrupt?

If you are a sales professional looking for a new role, consider thinking about each of these elements before accepting an offer. Braverman gives his two cents: “I think if you can use that combination of founder quality, founder-market fit, and then ideally, a founder entering a market that is either growing really quickly…or that is totally ripe for disruption…If you find all those things, consider giving [that company] a go.”

Leveraging Your Personal Network For Hiring and Getting Hired

Blond supplements Braverman’s advice with his own thoughts on great founders with an audacious vision, adding, “The ambition to build a big business I gravitate towards.”

He continues by pointing out that the power of your network should never be taken for granted: “Based on my personal experience, I can’t underestimate the importance of using your personal network, both as a candidate and as an employer.” Your network can be thought of in three categories:

  1. Investors: Your investors should be helping your business bring on talent for critical roles, particularly in sales. “If your investors aren’t helping recruit for you, I don’t think they’re doing their job,” says Blond. Of course, this applies primarily to senior-level and executive positions. 
  2. Former Colleagues: Many founders leverage their network of former colleagues to hire for sales leadership or individual contributors. If you are looking for a role in sales, this might be a valuable source to draw from during your search.
  3. Social Network: This might seem counter to traditional advice about not mixing personal relationships with business, but there may be promising opportunities with friends and acquaintances you trust. Use your best judgment.

Sales Recruitment Tips For 2023

For Job Candidates – Sales Leaders and Individual Contributors:

As a candidate looking for a job, if you are not in a position where you know the founder, you might need to take your time to assess whether the company you are applying for has real momentum or not. 

  • Relevance: Does the company you’re applying to have relevance to the current landscape? Is it serving the moment? But be cautious here: Some companies might have a temporary draw but don’t have long-term value.
  • Category Resilience: Braverman says, “If you’re going to join a company today as a seller, the most important question to ask is, ‘Has my category been negatively impacted by the new economic environment?’” For example, a B2B SaaS company that depends on other businesses thriving may have some difficulty in the current climate.
  • Scale Potential: How much can this business grow? Consider whether the company is already showing extraordinary growth or scale or if the roadmap projects to expand significantly as it evolves. To get an idea, review the data. Check growth month-over-month, and, especially if you are an individual contributor, check quota performances and take note of how often quotas are met and exceeded.
  • Career Development: For individual contributors, assess whether you have any potential for upward growth in the company. Do they tend to promote from within?

For Companies –– How to Stand Out to Top Talent

In an unpredictable economic climate, hiring quality sellers is essential to the success of your business. Unfortunately, many companies fail to incentivize their sales team and, therefore, may miss out on top-quality candidates.

In addition to creating a thriving business with impressive growth, opening paths for career development, and staying resilient, companies must focus on compensating their sales teams generously and fairly. 

Braverman suggests granting more equity to your sales team, not just the CRO or Head of Sales.  “It’s unbelievable to me how many companies don’t reward sales with equity. This is probably less true at the executive level –– sales leaders tend to do very well. We found that we had incredible retention at Flexport when we paired career progression with meaningful equity grants.”

Over time as a seller proves themselves, consider rewarding them with equity. This might be extra helpful in the event of a recession where you don’t have as much cash as you typically might in other circumstances.

Blond agrees that compensation is a very effective way to attract top sales talent and emphasizes more fair pay structure, particularly early in the sales rep’s tenure: “You have to remember when you’re hiring, especially individual contributors, many of these folks are living month-to-month…so joining a new company as a sales rep can be daunting and potentially prohibitive…based on the structure of the compensation during the first few months. One of the things we did at Brex and that I suggest for founders –– especially in the early days as you’re hiring…put [early sales reps] on a draw for 60 – 90 days.”

A draw means paying a seller their full commission for the first few months as they start at the company. It can mean the difference between hiring an amazing rep or losing them to another organization. 

Key Takeaways

  • Consider founder quality, founder-market fit, and market size to know whether a business will be successful.
  • Leverage investors to make introductions to valuable team members, and don’t be afraid to use your network to hire or get hired.
  • Compensate your sales team generously and fairly to attract the best talent. Use equity for high-performing ICs, and even consider restructuring your commission to give a runway for new employees.  

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