If only building yourself into the ideal sales leader were as easy as walking into a frozen yogurt shop. Imagine the vast selection of toppings you get to choose from: rainbow sprinkles, M&M’s, hot fudge and cookie dough bites. Each one adds a unique quality to the overall experience.
Some sales leaders deliver the rainbow sprinkles, while others offer the M&M’s — yet both bring valuable, colorful insight to the big picture. But even if you could pick and choose professional qualities in this way, which do you prioritize? How do you create a perfect melody of flavors when the combinations seem limitless?
Arjun Reddy, head of enterprise sales at Foursquare, doesn’t see sales leader qualities as something that can fit into a container. “I don’t think there’s a single formula for being a great sales leader.” He does, however, value his history of working with leaders who set their teams up for success and offer direct communication and empathy.
Although her top priority is providing her team with the support and resources they need to grow, Frontify’s VP of sales, Stephanie McSwiney, can relate to Reddy. “The most important duties of a sales leader, next to communication and empathy, are to enable, inspire and trust your team,” she said, adding that it’s rewarding to see how building trust benefits the team’s balance.
Built In NYC sat down with local professionals from the sales teams at Foursquare, Frontify and Checkout.com to learn how each of their career backgrounds have helped direct and inform their decisions as leaders on their teams. They also shared their thoughts on what qualities are most valuable in sales leadership roles. The only question that remains is: What flavor of sales leader will you be?
What is your career background, and how did it prepare you for a leadership role?
I’ve mostly had a business development background, focusing on strategic partnerships. I’ve also worked at a variety of different-sized organizations, ranging from publicly traded companies with large sales teams like AOL to Series A startups with only one or two sellers.
Caring about your team beyond their numbers creates a healthier, better sales environment — especially during the pandemic.”
What are the most valuable sales leadership attributes and characteristics?
I don’t think there’s a single formula. However, I’ve definitely noticed some common attributes among the great sales leaders I’ve worked with or worked for in the past.
The first is customer obsession. You have to understand how and why your products solve customer problems. This has impacts on a variety of things, including staffing and structure.
Next is setting your team up for success. Let the team know what matters and what doesn’t. Then find ways to free up their time, for example, by implementing tools that streamline Salesforce entry and shielding them from product or engineering discussions that might be time consuming or distracting.
The third attribute is communication. Direct — not abrasive — communication on performance, beyond just quota attainment, is really valuable.
And finally, empathy. Caring about your team beyond their numbers creates a healthier, better sales environment — especially during the pandemic.
What’s a recent example of how your leadership skills helped you or a colleague solve an issue?
We had a great enterprise seller working on a vertical that was not conducive to success due to questionable product-market fit. He had been laboring away with disappointing results, which he himself acknowledged. When I sat down and listened to the challenges he was facing, it was clear that a change had to be made.
As we analyzed historical deals we’d done and considered the challenges certain customers were facing, we realized that there was an obvious opportunity for this seller to refocus efforts into a different vertical. Having now spent more than three months selling into a new vertical, we’re already seeing exponential results from his focused pipeline generation.
What is your career background, and how did it prepare you for a leadership role?
My professional background is in business studies and communication psychology. Funnily enough, the latter has really helped a lot in my career. Communication is the most important aspect of leadership, other than empathy. Understanding stakeholders, prospects, clients and employees — as well as having honest and open two-way communication — is key.
I always worked in customer-facing roles while in school, from local ice cream stores to bars and pubs. I started my tech sales career as a sales development representative at Oracle and moved to an account executive role at BMC Software. After that, I really wanted to get into the nitty-gritty of tech, so I started consulting for implementation and solution partners of Microsoft. To round out my experience in the tech sales space, I wanted to join an early-stage SaaS startup. I was delighted when Frontify took me on as their 14th employee. The last four and a half years have been the most amazing journey. I never thought that work could be as fulfilling as it is at Frontify: amazing people, a visionary and brilliant product, and so many possibilities to learn and grow every day.
For a team to be fruitful and happy, they must have the freedom and resources to grow — both as individuals and as a team.”
What are the most valuable sales leadership attributes and characteristics?
For a team to be fruitful and happy, they must have the freedom and resources to grow — both as individuals and as a team. Giving them the support and resources to thrive and overachieve, as well as the chance to challenge the status quo, is what makes a genuinely great, transparent and efficient sales team.
Steve Jobs said leadership is about inspiring people to do things they never thought they could. In my experience, this requires integrity, the “practice what you preach” kind of stuff; humility, which makes you more relatable and effective as a leader; and a vision you follow full-heartedly with honesty, passion and never-ending positivity.
Trust all the members of your team, regardless of experience and seniority. Everyone has a valuable voice and opinion. They’re essential to the balance of the team. Sure, it’ll require time, empathy, good communication skills and an open mind — but once trust flows through the team, it’s extremely rewarding.
What advice would you give to someone feeling challenged in their sales leadership role?
Supporting the team’s growth from two people to a 40-person-strong team spread out across the globe in less than three years — while juggling family time and building a house — is probably the most challenging thing I’ve ever faced.
The best way to overcome this, in my experience, is to surround yourself with the right people — people who share your vision and trust you to lead them in the right direction, even if other difficulties arise along the way. Resilience is key: Focus on the solution and not the problem.
What is your career background, and how did it prepare you for a leadership role?
I joined WeWork when it was at a similar stage to where Checkout.com is now. Over the course of the three years I was with the company, we tripled our revenue and built our enterprise business from scratch. Coming from a company like WeWork, where we were focused on building best-in-class offices and workplace cultures, set me up for the exciting journey I’m on now at Checkout.
I was the third team member to join Checkout’s New York office, where we’re building a team and scaling our processes, while also expanding into new markets in a more operationally efficient way. Since joining, I’ve been blown away by the level of talent here. When you’re working at a fast-growing company, you may find your team members don’t necessarily come from industry backgrounds with extensive experience, but I’ve found that to be the opposite here. A lot of my colleagues have extremely sophisticated knowledge of payments, and I am learning a lot from them every day.
What are the most valuable sales leadership attributes and characteristics?
The first is being consultative. In a category like payments, where we are so critical to the day-to-day operations of our clients, deals should never feel transactional. We build partnerships with our merchants. This is not limited to the leadership layer — it is true across all levels of sales.
Second, it’s important to have a clear understanding of the problem. The best way to discover this is through asking the right questions. Behind every deal are people trying to do a great job and make their company better. Many times discovering personal motivation is just as important to sales as business motivation.
Lastly, being a good collaborator — someone who people internally want to work with — is massively important. To execute any sales strategy effectively, you need many different departments to come together. If you can’t work with coworkers, it will be very difficult to deliver for clients. This is in part why we put such a strong emphasis on team building and office culture at Checkout.
Interested in applying? Checkout.com is looking for people to join their NYC team who:
- love change
- are innately curious
- are excited to push their thinking
Speaking of collaboration, can you share an example of how your team came together to solve an issue?
We recently had a product strategy workshop focused on one of our business models. We brought together our commercial and product leadership teams to co-design a strategy to solve some of the most pressing challenges our merchants are facing.
What we produced in that session is now the cornerstone of our 2022 roadmap. It was an incredibly efficient and collaborative session because of the people on our team: individuals who are ready to challenge the status quo and excited to work closely with colleagues from different backgrounds in a fast-paced environment.
