All great sales leaders had to get their start somewhere. Whether they worked their way up from an SDR role or moved over from another team, every sales leader has a story.
Sarah Young never specifically wanted to go into sales (something we hear quite often), even though she was told by others that she would be a great fit for a sales career. She took a job selling Cutco in college thinking it would be a short term, part-time summer job. Sarah liked the income opportunity and enjoyed talking with and educating consumers, but she never intended to be in the role for long. Her dream was to work in the nonprofit space and make an impact in people’s lives.
However, after having quite a bit of success as a sales rep and then a manager during her time at Cutco, her eyes were opened to the possibility of making sales her long-term career goal. In addition to the income potential and the ability to help individuals, Sarah loves that she can directly add value to a business and the stakeholders she works with on a daily basis.
Now, nearly 10 years after college, Sarah has worked her way up from a Cutco rep to a sales leader at Springbuk, the leading employer-facing Health Intelligence platform, where she is Director of Sales Strategy and Operations. We hope you enjoy our conversation with Sarah about her journey from a sales rep to a sales leader!
In the 5 years you’ve been in tech sales, what has changed the most in terms of your buyer?
Unlike many veteran sales leaders, Sarah has a unique perspective as she’s spent only a handful of years in the technology field. Even still, a lot has changed in a short amount of time as software continues to evolve and as prospective customers are bombarded with more and more information than ever before.
“One of the biggest things we see is this trend of consensus buying. No longer do individuals want to make a decision on behalf of their organization, even if they’re completely bought in. Instead, they feel as though they need to bring in peers, managers, and others from across the organization to validate a purchase decision,” shared Sarah.
Sarah has also seen an uptick in the reliance on referrals from other customers, which plays hand in hand with software growth. With so many available options, customers can be paralyzed by the choice and want someone else from the industry to vouch for not only the software, but the team, the process, and the company as a whole.
What made you decide to move from being an individual contributor to a sales leader? What did that transition look like?
Sarah knew based on her previous experience as a sales manager with Cutco that she wanted to get back into a leadership role. She’s always been energized by creating a higher level structure and strategy and also empowering others to be successful and achieve their goals.
“It’s exciting to achieve your own goals, but it’s even more satisfying to help others grow and achieve their personal and professional goals,” she shared. It’s certainly more challenging since it requires an elevation of your organization, preparation, communication, and time management skills. Priorities shift toward advocating for your team, largely internally, and acting as a bridge between leadership and your team. Your primary responsibility as a sales leader is keeping reps constantly motivated and accountable to reaching these goals.”
“Part of this need to elevate your skills is a result of being in a position as an example. This can be a difficult transition and balance to strike between being relatable, yet still creating the necessary separation between you and those you manage to be an effective leader,” she says. In a rapidly evolving SaaS company, Sarah is constantly evaluating herself to ensure she’s growing and prioritizing the right things to in turn help her team grow and achieve goals.
Being a sales leader isn’t easy. Being on the leadership team at a rapidly growing SaaS company in an evolving market means that Sarah needs to evaluate herself constantly, be more prepared, manage her time better, and advocate for her team internally – all of which can be challenging endeavors. “At the end of the day, you have to become an example. This can create a separation between you and those who you are managing, which is why finding the right balance between being relatable and being an example is so important.”
Looking back on your journey, what were the tangibles and intangibles that helped most with your transition?
When Sarah reflects on her transition from an individual contributor to a sales leader with a significant amount of responsibility, there were a few important aspects that made the transition much more seamless than it would have been otherwise. While Sarah did gain managerial experience early on in her sales career – something not many are fortunate to receive – one of the biggest factors Sarah credits is the examples of those around her. Sarah has been able to identify the characteristics that make up a good leader and those that make up a poor leader. When she made the transition to her leadership role at Springbuk, she was able to adopt the characteristics that she admired in other leaders and work on refining skills that weren’t as developed.
“One of the most important things leaders can do is surround themselves with a great network of others that they can learn from and rely on,” said Sarah. “It’s important for me to have mentors and peers who are going through similar challenges at other companies. This way, we can help each other through those times and come out as better leaders on the other side.”
How has your experience as an individual contributor helped you as a leader? Has it made it more difficult in any way?
Since Sarah had literally been in her reps’ shoes in prior roles, she’s been able to really empathize with challenges and also give guidance on how to succeed in the day-to-day grind. Her unique perspective helps her relate to sales reps.
However, moving from an individual contributor to a sales leader hasn’t always been easy for Sarah. “It can be difficult when I empathize with their perspectives but am not necessarily able to provide the result they want because there may be a higher level decision that has been made. Being the ‘middle man’ can be difficult as sometimes I’m just the bearer of difficult news.”
If you were to give advice to an individual contributor that believes they have what’s necessary to become a sales leader, what would you tell them?
Often times, high-performing individual contributors don’t know how to articulate why it is that they are so successful in their role as a sales professional. This is why not all team members are fit to become sales leaders.
Though Sarah could articulate what it was that made her successful in prior individual contributor roles, she knew she needed to continue developing her communication skills so she could effectively lead her team. “In order to do this, I need to be a clear communicator and understand various sales frameworks so I can articulate which approach(es) are best for my team,” explained Sarah.
The advice that Sarah gives to those that are interested in a sales leadership role? “Know your why!” Why are you interested in this role? Is it the earning potential, the managerial aspect, the desire to develop strategy, or something else entirely?
Before raising your hand as a candidate, Sarah recommends spending as much time as possible with a current sales leader to understand specifically what they do on a day-to-day basis. While the title may sound appealing, there is a lot more to being a leader than managing individual performers.
“Get very specific about why you want to be in leadership, what motivates you to be in the role, and what you hope to accomplish, explained Sarah. “You must also be self aware and know your strengths, weaknesses, and areas where you need specific development. It’s no secret that stepping into a leadership role will increase in pressure, time commitment, and responsibility, so it’s not a decision to take lightly. If you believe you’re capable and ready, though, leading a team can be incredibly rewarding.”
What resources have helped you along the way?
There’s no better person to recommend resources than someone who has walked through the path herself! Sarah is a big believer in immersing herself in learning new frameworks, tactics, and managing practices. Here are two of her recent favorites books:
Ready to Learn More?
For more information on best practices of great sales leaders, check out the Costello resources below. If you’d like to see Costello in action, request a personalized demo of our real-time sales playbook software.