How to Scale Your Sales Team Quickly
Startups and other fast-growing organizations face a common challenge: In the early days of an organization, people join because they’re passionate about the mission. Yet too often, as the team grows in size, the tether to the original vision weakens, and new salespeople aren’t as successful as those who were there from the beginning. To ensure your new team is as passionate as your original team, leaders should follow these three tactics: 1) establish storytelling as a company norm, so every sales member carries your mission into customer conversations; 2) institutionalize deep discovery into your sales process, teaching new salespeople to ask strategic questions to understand customer goals; and 3) invest in human-to-human sales enablement, which provides the team with the assets to win business, including presentations, market data, tech tools, and a well-organized pool of case studies.
When Chief Revenue Officer Steve Johnson was ramping up the sales team at Hootsuite, he faced a big challenge: He needed to scale sales, and he needed to do it quickly.
As a veteran leader of previous startups, Johnson knew that growing sales fast would require new systems, processes, and infrastructure. He also recognized that he needed to scale the passion and belief that had propelled Hootsuite’s early wins. If they were going to be successful, it was crucial that new team members have the same fire in their belly as the original team.
It’s a common challenge. In the early days of an organization, people join because they’re passionate about the mission. Young sales teams typically have a strong emotional tie to the founder(s), the product, and the impact they can have on the market. Close proximity to the founders and a clear articulation of the market problem the firm is solving create a compelling story that unites the early team. Yet too often, as the team grows in size, the tether to the original vision weakens, and new salespeople aren’t as successful as the founding salespeople.
This is an avoidable problem. In my work with fast-growth firms, I’ve seen first-hand that when leaders are intentional about embedding their mission and a sense of higher purpose into their culture, sales can grow faster.
Johnson was proactive about three things: 1) building widespread belief in Hootsuite’s purpose, 2) institutionalizing processes to help new team members understand the positive impact their solutions could have on customers, and 3) providing a heavy dose of sales coaching. This work paid off: Over a two-year period, his team grew from 27 people in Canada to more than 1,000 people around the world who delivered a cumulative revenue increase of more than 56,000%. After 24 months of rapid growth, they announced one of the largest software raises in Canadian history ($165 million) followed by another $60 million 11 months later. Johnson went on to scale teams at Vidyard and Intelex, and is now COO of Berkshire Grey, the world’s largest robotics company.
“When you’re small and growing fast, you’re under a lot of pressure,” Johnson says. “You think you don’t have time to worry about seemingly soft concepts like culture, and belief, but building a strong emotional infrastructure enables you to scale faster.”
Whether you’re trying to scale sales to take your firm public, recover lost revenue due to the pandemic, or step into new opportunities, being intentional about helping your sales team understand your organization’s larger purpose and the role they play in delivering on that for customers provides the bedrock for revenue expansion. Here are three ideas you can embed into your foundation to ensure your new team is as passionate as your original team:
1. Establish storytelling as a company norm.
“Great companies are built on great stories,” as LinkedIn founder Reid Hoffman recently said on his Masters of Scale podcast. Early sales teams have a clear sight line to customer impact. They understand why the product and the company exist, and they carry that passion into customer conversations.
As the sales team expands, you can ensure that you keep this emotional tether strong by consistently weaving stories about how your offering makes life better for customers into your onboarding and making it part of regular meetings. For example, when we worked with Steve Johnson scaling the Hootsuite sales team, we trained sales managers to start each weekly meeting with a story about how their solution made a difference to customers. This enables new hires to deepen their understanding of the product impact, and it strengthens their connection to the founding vision. This makes them more effective in customer conversations.
2. Institutionalize deep discovery questions in your sales process.
A fast-growth sales team who is excited about their offering is at risk for employing what we refer to as the “spray and pray” model of selling. Excited sellers spray the pitch out there as fast as they can and then pray that some of it sticks with the prospective client.
While well intended, enthusiastically pitching solutions with little or no customer intelligence is unlikely to win large deals, and long term, it puts the organization’s reputation at risk.
You can avoid this trap by building deep client discovery into your sales process. Teach new salespeople (and managers) how to ask strategic questions to better understand your client’s goals. For example, you want your sales team to understand your customers’ market environment, what their most pressing challenges are, and how they have defined success for themselves. Asking the customer questions like “How does this area of the organization (the space where your solution could help) impact your larger strategy? Or “What effect would these improvements have on your long-range goals?” helps your sales team understand the potential ripple effect of their offering. Asking insightful questions about the customers overall goals (versus just your solution) is rocket fuel for a young sales team.
When salespeople ask prospective clients good questions, the sellers improve their business acumen quickly because they’re learning about the market from the customer’s perspective. It also helps them build better customer relationships before there’s a major deal on the table.
Institutionalizing deep discovery questions (before pitching) sends a collective message to the sales team and the market: We want to know what’s on our customers’ minds.
3. Invest in human-to-human sales enablement.
When a company is growing quickly, sales managers are under pressure to hit big numbers. This can (unintentionally) hinder skills-based sales coaching. A sales manager with a stake in the deal is often tempted to take over a seller’s sales call instead of providing backstage skills coaching. While this may win the deal in the moment, it doesn’t scale. It also put the organization at risk for becoming transactional, because sellers don’t learn how to make a compelling case for the solution on their own.
Instead of relying exclusively on sales managers (who may be inexperienced or overwhelmed) you can scale faster by building a human-focused sales enablement function. Sales enablement — a concept forged in the startup world — traditionally focuses on providing the sales team with the assets to win business, including resources like presentations, market data, tech tools, and a well-organized pool of case studies. Fast-growth firms take the enablement concept to the next level by adding a strong sales coaching function.
This takes (some of) the pressure off the sales managers by providing reps with support from someone isn’t under the same deal-to-deal pressure. When a supportive third party (the coach) works with the individual sellers on skills like: opening sales calls based on client issues, deepening discovery conversations, and sharing the company story in a compelling way, it shows the sales team, it’s not just closing the deal, it’s how you close the deal.
A human-to-human coaching program can accelerate the team’s passion for customers and give them the skills to authentically demonstrate that passion throughout the sales process.
When the pressure is on to grow revenue, it’s tempting to focus on concrete tasks like systems and processes. However, the firms who build sustainable revenue are also intentional about the more emotional elements. Use these three techniques to make sure that your growth doesn’t dilute the secret sauce that got you started in the first place.