The Ultimate Guide to Hiring Sales Leaders

The Ultimate Guide to Hiring Sales Leaders: Uncover the Secrets to Building a High-Performing Sales Team

The estimated reading time for this post is 8 minutes

A few months back I had an insightful conversation with a private equity investor who experienced the challenging economic times of 2001 and 2008. Over the last year, he has interacted primarily with GTM teams and startups in the SaaS tech sector.

Many of these ventures are run by first or second-time startup founders and executives who, in the past 10 years, haven’t faced the challenging sales environment that we currently find ourselves in. Quite frankly, it can be tough to adapt if you haven’t previously weathered a market storm. 

Kevin Chiu, co-founder of Catalyst, highlighted this notion in a recent LinkedIn post: 

There’s no magical solution, no miracle cure. It’s about more than just product-led growth, inbound leads, renewals, strategies, net-new revenue, EBITDA, expansion, retention, or overall revenue to win in today’s tough market. It requires managing EVERYTHING

Thriving, resilient businesses operate as interconnected ecosystems, not isolated silos. 

Startups that adopt a comprehensive, integrated business approach are the ones that will weather the storms and come out stronger. But how can they achieve this?

Navigating the Shifting Landscape of Sales Leadership Hiring 

In my work advising founders in the early stages of their companies or established small business owners, a recurring theme is the need to replace senior sales, marketing or customer success executives. These types of decisions are easy or  straightforward, because, as your favorite mutual fund disclaimer says,  past performance doesn’t guarantee future performance and the ability or willingness to stay competitive in the current fast-paced environment. 

This issue arises due to several reasons, not limited to: 

  • Inflated titles that aren’t backed by proficiency required at that level
  • Over-compartmentalized go-to-market functions with the entire Revenue Operations teams
  • Staff turnover due to more promising opportunities during challenging periods
  • A tendency to overlook internal talent development in favor of sourcing a competitor’s top talent
  • Inconsistencies in expectations or presumptions relating to performance
  • Regular changes in execution strategy that are not based in fact or the inability to execute due to internal constraints

These reasons contribute to the development of a daunting skills gap. This gap subsequently diminishes the pool of leaders equipped to rise to the challenge, persist and flourish. 

Not too long ago, the vibrant job market allowed even the not-so-skilled ‘B and C-players’ to achieve significant results – a proverbial “rising tide floats all boats”. This environment made recruitment of any caliber of talent challenging, resulting in some employers skipping vital parts of the hiring process. 

This is a sentiment echoed by investors I’ve spoken to, who observe that yesterday’s ‘A’ investment often gets rated as ‘C’ today.  As can be attested to by the number of SAFE, down-rounds and flat-rounds which have been floated over the last twelve months. 

Imagine being groomed in an environment focused on high-speed SMB inbound sales as a BDR and eventually being promoted to the VP of Sales for inbound teams. This environment is your comfort zone and forms the basis  for your hiring, onboarding, coaching, and forecasting. 

But what do you do when a new outbound strategy needs to be created or the need arises to pivot into a different market segment?  If you’ve not been updating your skills, your historical experience will not assist you in the execution of this updated strategy.

Leadership at Each Stage of Development

Much like people, businesses have their own cycle of life – they are born, they grow up and then eventually retire and die.  But unlike people, organizations have the potential to live forever (few live past a hundred years) if they have the right leadership at each stage of their development.

When a company begins its journey (usually called a ‘start-up’), it needs certain types of personalities, skills and abilities such as creativity, resilience and stridency are required to overcome challenges and roadblocks.  They need to be agile enough to iterate their product to fit the market, open enough to listen to prospects, mentors and strangers, and stubborn enough to push for their vision.     

As the offerings gain traction with the market, a new type of leadership is required.  One that is focused on creating proven and repeatable outcomes.  Often if the owners or founders are unfamiliar with these methods, they’ll learn how to surround themselves with individuals who can assist them in accelerating this forward momentum.  As a result the focus on systems, processes and people become more increasingly important to scale the growth.

When the company has gained substantial market share, it will require even different leadership characteristics.  These leaders will be more adept at expanding offerings into new geographies or industry segments in a proven and repeatable way.  In addition, broadening the product offering for current customers is thought as a proven way to ensure greater recurring revenue generation, so a senior product leader is as important as other product offering leaders.

It’s likely that your current leaders will not be present for the entire journey of the organization.  Most famously, Steve Jobs and Bill Gates were removed or left during their respective company’s development.  So don’t be surprised if, at some point in time, your founding team is no longer present at the company.

During the start and scale up phases of the organization will need a war time sales or revops leader because they need to be able to quickly build tactical battle plans and engage with the market.  During expansion and traction stages a peace time revops leader will help ensure that market share is maintained while expanding into new markets at the same time.

Be Clear on WHY 

Prior to bringing a new hire onboard, particularly in a role as crucial as sales leadership, it’s imperative that you clearly identify the following: 

  • The motive behind the hiring decision
  • The responsibilities essential for the role
  • The definition of success and the roadmap to achieve it
  • Valuable lessons learned from previous hiring scenarios
  • Your contribution towards their success

Once these points are crystal-clear, deploy a hiring scorecard and stick to a tried-and-true hiring process

Thinking that you’ll instinctively know a good candidate when you see one, trusting solely on your intuition, or figuring out the hiring process in real-time are traps that could initiate a cycle of expensive hiring mishaps. Instead build a recruiting and talent acquisition machine that provides for repeatable outcomes and attracts high quality candidates.

In the startup and scale up phase, you may find that you need specific functions and activities completed that do not require a ‘’full time” employee.  Using fractional or part time personnel in these functions allows you to conserve capital while receiving the benefits of this high level of expertise.  So instead of hiring a full time Finance, Marketing, Sales or RevOps leader, consider another path until you think you can keep someone busy full time.

Pro Tip: Abandon the notion that it is acceptable to cycle through multiple sales leaders before landing the right one. Entering the process with a mindset that the initial hires will inevitably fail can breed setbacks for all parties involved. 

Embrace Unfamiliar Territory 

Diversity of people creates diversity of ideas

As noted by Bill Gross, founder of Idealab, who has been involved in 300 rounds of financing and 35 successful exits since 1996, founders often gravitate towards hiring people similar to themselves for ease of communication and rapport-building. However, research from Boston Consulting Group points out that companies with diverse leadership teams witnessed a 19% rise in revenue compared to companies with homogeneous management.

So when you create a workforce where your team comes from varied backgrounds, educations and cultures you then create advanced opportunities for learning.   When everyone is aligned according to the shared vision and values then the growth opportunities are limitless.

Be Comfortable being Uncomfortable

Engaging with the world on a variety of levels requires you to be comfortable about being uncomfortable.  Because you want to know all the answers and won’t know all the “right” actions for each decision.

So learn to live with not knowing all the facts before you make a decision and appreciate that we are striving for Progress and not Perfection in all of our interactions.

If your RevOps leader does not exhibit these characteristics then, depending on your stage of the business cycle, you may not be ready for that person.  How do you test for this?  Place your candidate with an uncomfortable decision and see what happens.

Be Authentic

Today’s employees understand that they’re not going to be at your company for life.  Even if you provide them with all the tools and training they need to be successful they’ll eventually seek other opportunities or you’ll need different skill sets or attitudes as you progress through the business lifecycle.

It is therefore crucial that you be honest and authentic to your market.  Meaning that all of your outward communications should be reflective of your core values and beliefs.  A great recent example is the debacle that happened at Carta with their secondary marketing group.. Instead of making excuses for that group’s poor execution, Henry Ward, Carta’s CEO apologized and then shut down the business entirely.  Because, for Ward, being trustworthy is the most important part of his authenticity.

In Conclusion 

As a small business owner or founder understanding the type of leadership you need to hire for your current stage and scope of your business is essential.  When you hire the right type of leaders in the right roles you not only conserve your capital you can also accelerate your growth.

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