How to Build — And Scale — A Successful Sales Team

by Janey Zitomer
November 22, 2019

Tesla’s mission statement, “accelerating the world’s transition to sustainable energy” not only aligns well with consumers’ view of what they do, it also meets team members’ expectations in terms of what they were hired to accomplish. 

We recently spoke to four Boston sales leaders about that crucial point in time after signing a key recruit. They told us how they encourage new employees to incorporate useful strategies from previous roles while setting the entire team’s sights on the same mission. 

 

Rapid7 team

Matthew Cappello, regional vice president of sales at Rapid7, knows his audience. He leverages sales employees’ competitive natures to create an environment that’s challenging but supportive. 

Their insight cloud offers customers full visibility into their connected environment, providing analytics and automation so that users can focus on their business’s main mission rather than thwarting cyber attacks. 

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

Our three fundamentals are our investments in our people, sales enablement and process. It really starts with hiring and attracting the right talent. We have found that sales representatives with high levels of self-awareness give our teams the ability to be more prescriptive with both our sales enablement engine and management techniques.  

It takes the guesswork out of individual development plans and creates a trusting environment for representatives to take disciplined risks knowing that management will throw the rope back over.

Lastly, sales is a numbers game. Utilizing internal and external sales tools, we baseline and track progress so each representative knows where they stand at any point in time; not only from a numbers perspective but also in terms of individual development. 

We look to empower our managers and representatives to carry on the company’s core values.’’

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

When scaling teams, it is imperative to have a shared common mission. It creates a culture of teamwork regardless of whether you’re an individual contributor or sales manager. We look to empower our managers and representatives to carry on the company’s core values.

We also recognize that effective sales training is not a one-shoe-fits-all approach. Each seller who joins Rapid7 is at a different stage in their journey and each stage requires a different approach. We pride ourselves on being flexible and adapting to the requirements of our sellers in order to provide relevant training based on their skill sets. We have a coach-first mentality, which creates a trusting relationship throughout the organization. 

Recognize that most sales representatives are inherently competitive. We encourage and promote as much healthy competition as we can. From pipeline competitions to enablement pitch offs, we try to keep the sales floor as entertaining as possible, driving a better work experience.

 

datadog
datadog

Datadog is mission-first and mission focused. Petra Ross-Raymond, director of sales development, told us that their blueprint for scaling the department relies on a solid foundation. 

The monitoring service abides by the theory that increased system visibility leads to further success. And at Datadog, that applies to their culture and their product. Just check out their aggregated metrics and events DevOps stack. 

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

My blueprint starts with a clear mission, preferably developed as a team and influenced by key business partners. The most rewarding teams I’ve been a part of work with a sense of purpose; we can see how our efforts impact the greater goal. Foster a culture of knowledge-sharing to level up everyone’s skills and multiply your impact as a group. Look for opportunities to work closely with other roles who share your mission. 

As you scale, you may need to evolve. Be prepared to ask, “Does our mission still align to important greater goals? How are we collaborating with each other and with our business partners?”

The most rewarding teams I’ve been a part of work with a sense of purpose.’’

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

Once you’re part of a successful team, you want to maintain what’s working. However, scale does require flexibility. High-performing teams will thrive through change when the team is aligned to a mission, when they understand how and why strategy is changing, and when they have a clear sense of what new skills or activities will be required for success.

 

smartsense employee
smartsense

Culture is a reflection of not only the people who deliberately create it, but also anyone who contributes to a company as it grows. But culture isn’t the only thing leadership at SmartSense by Digi monitors.

The IoT solution allows users to track food and pharmacy safety and supply chain visibility. VP of Global Sales Jeff Melvin told us how his team mirrors the business’s overall vision and drives quality control.  

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

We are looking for people who want to be part of the adventure that comes with building a growth-stage technology company. This includes self-starters, motivated, passionate people who want to be part of a fun, dynamic and ever-changing environment. Employees need to fit into the culture that has been created while adding their own fingerprint. We look for team players who strive to make others around them as successful as they’ve become.

We look for team players who strive to make others around them as successful as they’ve become.’’

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

Scaling requires a clear understanding of roles and responsibilities, as well as a defined selling process that will drive the most success while enabling people to thrive using the skills they have brought to the table. Training is constant, as change is constant. Finding people who thrive in that culture is key. A constant drumbeat of hiring must be part of the culture or the sales team won’t be able to accomplish the growth that the business demands.

 

Alyce sales team
Alyce

We all have an area code or number memorized for the purpose of being able to ignore yet another telemarketer.

Alyce is on a mission to turn that annoyance into value by offering one-to-one gifting, swag-select options and tracking benefits for businesses. Head of Sales Michael Goldenberg shares how he builds strategies tailored to individual challenges, below.    

 

What’s your blueprint for building a sales team?

When you’re building out a startup sales organization, you can most certainly try to avoid the mistakes and headaches you’ve seen created in other roles. But even that is a fool’s errand because you’re being led by biases of previous experiences instead of the specific scenario at hand. Much like a tiger and turtle survive and thrive differently, so does each startup sales organization.

Building a startup sales team is more like cooking. There are certain principles of balance you can expand upon. In sales, you want to balance good hard-working people who have enough experience to succeed quickly with enough hunger to push hard. You want to build a process that guides but doesn’t restrict. You want to build a set of tools that empowers but doesn’t paralyze. And perhaps most importantly, you want to build a culture of high performance that doesn’t burn out the people you depend on most.

 

How did you identify these keys and how have they made an impact as you build a team?

I identified most of these things while watching other people try to take their previous successes in other companies and industries and run that same playbook in an entirely different circumstance. I also learned many of these lessons from messing up myself, often trying tactics I took from other people only to find out they didn’t apply to my scenario. 

Don’t assume what has gotten you to the top of the hill is enough to get you to the top of the mountain.’’

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

Once you have that fire started, keep adding to it. Don’t settle for the logs that are already there. That means doubling down on your efforts to hire, train, support and continue to maintain performance. Continue to emphasize the need for the team to continue to evolve and improve. Don’t assume what has gotten you to the top of the hill is enough to get you to the top of the mountain.

Build a strong foundation of people and culture so those employees have a stake in cultivating and shaping the future hiring and team enablement.

 

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