Hiring a Sales Leader (Part III): What Level Should I Hire For?

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This series outlines best practices to find and recruit a top-notch sales leader for your company, in three parts:

Read on for insights on making the best leadership hire for your company's needs.

On their journeys from being StartUps to ScaleUps, every one of our portfolio companies has had to hire sales leadership. One of the most common questions we are asked is: “At what level should we hire our sales leader?” Depending on your needs and stage of growth, it may make sense to hire your sales leader as a CRO, SVP, or Vice President. Posting the role at the right level is critical to attracting, engaging, and hiring the right candidate in an efficient hiring process.

We encourage you to begin by looking at your short-term revenue goals and business needs. As we mentioned, planning for more than the next 24 months is one of the most common mistakes ScaleUps make when hiring a sales leader, when goals and growth can change rapidly. In the next 12-24 months, what will your sales leader need to accomplish, and what tradeoffs are you willing to make to get there? 

Creating a structured and intentional approach to hiring ensures you vet candidates for the skills that matter and avoid intuitive biases. At Insight, we focus on 5 core competencies in a sales leader, which can vary based on level of experience: 

  • Core Selling Skills – A strong understanding of how to identify and access decision-makers and navigate prospects and accounts to get to a sale. This includes tactics like discovery and value-based selling, but it can also mean rolling up your sleeves and working to close a specific deal.
  • Sales Enablement – An understanding of the appropriate processes, training material, and support structures (such as deal desks and solutions engineering teams) to support the designated sales motion, and how to build them.
  • Metrics / Process-Driven Sales Management – A  scientific approach to the management of the sales organization, leveraging data such as stage velocity, pipeline creation, and account potential to manage day-to-day activity and conduct annual planning.
  • Go-to-Market Strategy – Your ability to identify the appropriate sales motion for their company and structure the organization around that, as well as a strong grasp on the various types of sales channels for each sales motion. For more demanding leadership roles, it can also include targeting, segmentation, and developing a value proposition. 
  • Team Building, Development, and Coaching – A history of building strong teams both through recruitment and team development, as well as coaching and leading organizations to optimal performance.  

For each Sales Leader level – CRO, SVP, and VP – there are, of course, many variations on levels of expertise. Below, we share a general blueprint on what to look for when making this mission-critical hire. If you are a sales leader or someone in an individual contributor role with hopes to grow in leadership, the below will also be a useful guide on the areas to continue to grow and develop throughout your career. 

Now let’s break down the range of competencies we see at each level, so you can make the right choice for your team.

CRO

CROs are the highest level of sales leadership, with the ability to partner well across the organization to build the processes that will grow the company not just for the long term. They have experience across all core competencies and a strong understanding of how product marketing, customer success, and sales work together to drive revenue. CROs need to not only be able to close a deal, but also design a sales strategy and organization, including a GTM strategy and a vision of what sales enablement might look like in a new organization. 

In addition to competency in all these key areas, we also generally see experience: 

  • Managing 10-50 people if not more (depending on the size of sale).
  • Repeatedly building a sales organization (1-3 times) or has built out a highly successful segment sales organization.
  • Creating metrics-based modeling for comp and quota design and capacity planning.

SVP

This role is typically for a more experienced operator who may have either run a full sales organization or who may have led a large team in a sophisticated sales organization. They can design sales strategies, develop and manage large teams, and take a metrics-based approach to decision making, with a strong POV on the right metrics to drive sales behavior. Unless they have worked at sub-$20M company, they may not have extensive experience at GTM strategy, designing training programs, or developing an account potential model to design territories and quotas. However, they will have experience interacting with and executing on these projects and understand the fundamentals enough to start building them with support from sales operations. 

VP

This is the role that is most ubiquitous. In larger sales organizations, VPs are often leaders who may manage a regional or divisional sales team. In early-stage companies, these are often the first sales leader that the company is hiring. They should be good managers but may not be as strong at managing through layers. VPs need to have a strong ability to roll up their sleeves and work on deals (in early-stage companies they may even be a player/coach). They need to be able to quickly determine a strategy for their team, perhaps design the first set of playbooks for the organization, and then staff up the team. Often, this might be a good opportunity for promoting an up-and-comer who has a strong metrics-driven mindset within the sales function.

It’s all about organization fit 

As you develop your job posting, consider the specific needs of your organization and create the responsibilities for the appropriate level of sales leader that fits your stage. If you’re an early-stage scaling company that has a few sales reps and needs a leader, you should be looking for a VP-level candidate. If you post for an SVP or CRO, you’ll get candidates who are over-skilled and overpriced for the role. Over time, you may need to staff a leader over the VP of sales – someone who can craft a more formal strategy and GTM plan – and if you’ve overtitled the role of the VP, that will put you in the awkward and demotivating position to demote them to bring in an SVP or CRO.

We know that assessing skills can sometimes be more art than science, and we don’t want to remove that. As you go about your choice, use these standards as a kind of spectrum or barometer to help you set the right expectations. Careful planning and scoping out the appropriate job will help you find high-quality candidates quickly and build an organization that can continue to grow. 
 

Hiring a Sales Leader (Part I): 5 Common Pitfalls to Avoid

In case you missed them, review the other blogs in this series of making a successful sales leader hire.
  • Helen Hua

    Helen Hua, Senior Vice President, Talent COE

    Helen joined Insight in 2017 to lead executive networking, best practices and other executive talent initiatives across the Insight portfolio. Prior, Helen was a Principal at True Search, an international executive search firm. At True, she led and drove executive searches across scaling venture and private-equity backed technology companies…
  • Travis Kassay, Executive Vice President, Sales & CS COE

    Travis joined Insight in 2019 as an EVP on the Insight Onsite team. Travis partners with portfolio company CEOs and their leadership teams to build scalable and effective go-to-market strategies. Leveraging his more than 20 years of experience in sales, inside sales, and sales operations, Travis consults with portfolio companies to address…