In March 2015, Microsoft founder Bill Gates went on stage in Vancouver, Canada to give a TED Talk. Five years and 36 million YouTube views later, the presentation — titled, “The next outbreak? We’re not ready” — became heralded as an ominous portent of the Covid-19 pandemic.
The start of the decade was a tumultuous time defined by leadership success — or a lack thereof. Public authorities had to navigate an unprecedented catastrophe while managing lives, policies and the court of public opinion. People that had seldom seen the limelight, such as heads of health organizations, were thrust onto pulpits and given reins over the well-being of nations. Ultimately, Bill Gates’ portentous advice required individuals to step up and become leaders.
While sales reps of tech companies deal with much lower stakes than global health, a similar priority is given to leadership development for successful sales departments. Many key attributes touted by those that transitioned from individual contributors (IC) to leadership positions are universal — no matter the objective at hand.
Mathew Young, Miro’s head of strategic sales, cited empathy, curiosity and a growth mindset when asked about the skills he applied to his role. Others, like Ontra’s managing director, Jeffrey Herscott, pointed to more specific hats that sales leaders should wear, such as that of a good listener, a thought leader and a people manager. Performance metrics go a long way, but some that have made the transition emphasize the ability to be noticed as an important step before independent sales reps can make the leap. “Your personal brand will spark when you are yourself,” advised Pablo Talarico, Qualtrics’ regional sales manager.
The path to leadership doesn’t have to be a lonely one, either. Managers remain the most direct and steadfast ally for sales reps within an organization, and ICs that keep them informed can jumpstart the process. “It’s hard for an ISC who hasn’t been a leader before to self-identify ways to build leadership skills,” said Matt Mason, SmartAsset’s VP of sales, “So lean on your manager here.”
Developing such interpersonal relationships is an all-encompassing endeavor. For Jacob Buckland, Yieldify’s VP of sales and services, that ranges from broad strokes — “all good reps build relationships with their prospects” — to daily interactions, such as understanding “tone, mood and facial expressions.”
Whether it’s an influential tech figure giving a TED Talk, public health officials molding public policy or a sales rep helping their team hit revenue goals, leaders are essential to organizational success. For a closer look at the drastic leap from IC to people manager, Built In NYC spoke with sales leaders for their advice on how to land the promotion.
Miro is an online collaboration platform that offers a whiteboard tool for distributed teams to work together. For a B2B company of 1,800 employees that is spread across four offices, sales leaders are crucial for team alignment and problem solving, backed by a robust framework in place for leadership development and transition.
Before you moved into sales leadership or management, how did you build your leadership skills as an individual sales representative?
The transition from individual contributor (IC) to first line sales leader is a challenging one. Thankfully, there were a few things I did to prepare myself, which made the transition a little bit smoother.
Internally, I would look for opportunities to take on leadership responsibilities and shadow my manager wherever possible. This included volunteering to run team meetings when my manager had a conflict and spearheading a sales-wide pipeline generation committee that met on a monthly basis. Basically, I would look for an area where we were struggling as a team or sales org and volunteer to help take that problem on with a group of my peers.
Shadowing your manager is something people don’t always think of. It can be very valuable as you get to see all of the little things that they do on a daily basis that you might not have visibility into otherwise, like watching them build out their forecast and report it up.
Finally, I was fortunate that most of my employers offered leadership development courses that my manager nominated me for. These were very valuable. If your employer doesn’t offer such courses, there are several that you can sign up for externally.
Take initiative and don’t be afraid to fail.”
What sales skills have been most applicable for you since you moved into a leadership position?
First, I try to approach every situation by putting myself in the other person’s shoes. How would I feel if I were them? What questions would I ask? What would I care about? If you can do this effectively, it is game-changing, whether you are dealing with a customer, a peer, your boss or a direct report. The key is to care though, you can’t fake it.
Secondly, being genuinely interested and curious about the person you are speaking to allows you to do much deeper discovery and truly understand their challenges and motivations. This helps you solve problems and prescribe solutions that are relevant, creative and impactful.
Lastly, I find that the best sellers and leaders are never satisfied with their outcomes and are always looking for ways to improve. It’s not that I don’t celebrate success. I just believe that there is something to learn from every engagement and interaction, even if the outcome was positive. Sometimes you execute really well and lose, and sometimes you execute less effectively and win. Therefore, if you treat everything as a learning experience, it will lead to more predictable, long-term success.
What advice would you give to a sales rep who’s dreaming about attaining a leadership position someday?
Take initiative and don’t be afraid to fail. It will help you get noticed and also give you experience leading teams and handling complex problems.
Most importantly, work with your manager to build an individual development plan (IDP). An IDP should include the top three to five skills or areas you need to work on to be considered for promotion. Be sure to prioritize the key aspects of the role or business that you are least familiar or comfortable with. The IDP should also include how you will measure progress and should be reviewed together with your manager on a regular basis. This ensures you remain aligned on your progress and overall readiness.
Finally, find a couple of mentors. Ideally, one internally and one externally who can help groom you and develop a well-rounded perspective.
Ontra is an AI-backed platform for legal contract automation and intelligence with a network of lawyers around the world. The scalable software solution streamlines more repetitive legal processes and manages contract data. As a software company that sells its product to legal clients, Ontra relies on an organized sales team with strong leaders to support its business model.
Before you moved into sales leadership or management, how did you build your leadership skills as an individual sales representative?
Fortunately, before I joined Ontra, then known as InCloudCounsel, I’d had a taste of leadership. While practicing corporate law at Simpson Thacher & Bartlett LLP in New York as a mid-level associate, I delegated certain tasks — such as managing a closing checklist and communicating with lawyers at another law firm — to more junior lawyers. Though I wasn’t their direct supervisor, it was a good learning experience on what it takes to be a good leader: delegating, providing feedback and setting the team up for success.
When I became the second sales director at Ontra, I was an individual contributor focused on closing as many deals as quickly as possible. Even as an individual, I found ways to lead by example. This meant tackling every task with 110 percent effort, which included keeping Salesforce current with well-organized call notes, engaging with as much sales literature as possible to become a thought leader and helping new hires better understand our products and target market.
At the end of the day, my job was to close deals, but the way I approached the job helped prepare me for a leadership role.
What sales skills have been most applicable for you since you moved into a leadership position?
A sales leader is a coach, an enablement professional, a thought leader and a people manager. Regardless of which role you play, three sales skills translate well to leadership: organization, persistence and listening.
Sellers and leaders must organize their day well. That includes keeping up with product updates, maintaining group meetings and Slack conversations, coordinating cross-functionally and using the tech stack effectively.
Sellers and leaders must also be persistent. They stay hungry and optimistic in the face of a thousand no’s. They stay motivated despite losing a massive account. They stick to their approach despite falling flat in a pitch. Leaders must also stay persistent — motivating the team when productivity is slow, working with closers who progress at different rates and staring down OKRs to achieve them.
Finally, being a good listener is invaluable. To effectively close deals, sellers must understand what motivates their prospects and what they care about. In the same way, leaders need to understand what their team and managers care about to effectively lead them. It starts with listening and then acting on feedback and input.
A sales leader is a coach, an enablement professional, a thought leader and a people manager.”
What advice would you give to a sales rep who’s dreaming about attaining a leadership position someday?
Organization is key for an individual contributor but even more so for a leader. You won’t become an organized sales leader and talented forecaster without taking care of your house, which includes effective outreach, constant communications with colleagues and excellent note-taking hygiene.
Be open and communicative with everyone. Listen attentively, and don’t be afraid to speak your mind in a healthy way.
Experiment through trial and error for continual improvement. Push yourself — and later your team — to improve, especially where they might feel discomfort, such as with cold calling and pitching. Try techniques you read or hear about. Never stop evolving because as soon as you get stagnant, you are less inspiring.
Don’t be afraid to let people shine. I am the conceptual leader of my team, but each person on my team is a leader in different ways: on product knowledge, sales best practices, the tech stack or something else. Deflect credit back to the people who are responsible for executing on the mission.
Hold your team accountable but let them know you will fight for them on the things they care most about. Always remember you are a resource to help them succeed.
Qualtrics is a technology platform that helps teams and organizations collect, manage and analyze experience data. With four core business pillars — customer, product, employee and brand — covered by its software solution, Qualtrics empowers companies to act on data insights. With businesses as the company’s primary clients, the sales department relies on a strong leadership development pipeline to maintain its customer base.
Before you moved into sales leadership or management, how did you build your leadership skills as an individual sales representative?
When I was a sales representative, I developed this vision that I was the owner of my franchise. The vision made me understand that I was accountable for my performance, so I took a leadership approach over my franchise in all the sales dimensions. From that point, I was seen as a leader, so moving to a leadership position was a natural move.
A concrete example of this was while I was an analytics sales rep in Argentina, I did an event for more than 220 people sponsored by more than eight partners, a great agenda including three customer’s presentations and one very good sports celebrity, Juan Martin Hernandez, one the best Rugby Players in history. In that one event I was able to develop a very strong personal brand, generate a pipeline, demonstrate the ownership I have over my franchise and leverage the business network I have developed.
Have a winning attitude and be aware that success is earned every day.”
What sales skills have been most applicable for you since you moved into a leadership position?
The decision criteria is the area where I have invested most of my time. Going from a sales position to a leadership role makes it hard to switch from doing to doing through the team. Also, you find yourself in a very challenging agenda where time management is crucial. In this scenario, working on understanding how to prioritize important and urgent tasks has been key for me.
The first months of my leadership role were mainly on the important and urgent quadrant. As months passed, I started very consciously leaving some urgent topics under my team’s responsibility, so I could take the time to start investing in the important and not-urgent quadrant.
What advice would you give to a sales rep who’s dreaming about attaining a leadership position someday?
Build and invest in your personal brand. Your personal brand will spark when you are yourself. Be verbal: Talk about your plans for the future. Develop a business network with stakeholders that may impact your development. Have results, but be able to show that those are a direct outcome of a plan. Lead from wherever you are, but be humble enough to learn and be led by others. For all of these, try to do it with the energy that develops an environment where people want to work with you.
In addition, have a winning attitude and be aware that success is earned every day. And when you move into a leadership position, keep that approach, but consider that you are now a coach of players with different motivations and unique triggers — that will help you build a winning vision across the team.
SmartAsset is an online hub for consumer-focused financial information. To help customers make better decisions, the company operates a marketplace connecting them with financial advisors and products. Internally, strong leaders on the sales team help drive the vision of SmartAsset as the go-to resource for financial advice.
Before you moved into sales leadership or management, how did you build your leadership skills as an individual sales representative?
I think it’s worth nothing that this all starts with making the decision that you want to be in leadership and ensuring you make that clear to your manager. The process of getting all the cards on the table on what you want to do within an organization allows for your manager to outline what steps you’ll need to take in order to be ready for leadership within your respective organization.
That said, the best thing I did to build my leadership skills as an ISC was build confidence and buy-in by taking on many of my manager’s tasks, such as sending out activity updates, running morning and afternoon huddles, presenting in our all hands and kickoffs as well as running trainings across the team. This allowed me to get a better understanding of the types of messaging that resonates and motivates a sales team and find my voice as a leader along the way.
Focus on what you can control, continue to develop and be patient — the rest will take care of itself.”
What sales skills have been most applicable for you since you moved into a leadership position?
The ability to quickly build trust through genuine and authentic communication is probably number one. A close second may be one many people don’t think of, but managing a pipeline effectively is something that is important as an ISC, but equally if not more important as a leader. However, as a leader, the pipeline is not composed of sales opportunities, rather it comprises tasks, projects, developmental feedback and follow up, among others. Different outcomes, but they have similar methodology in terms of staying organized and prioritizing.
What advice would you give to a sales rep who’s dreaming about attaining a leadership position someday?
Every day is an interview as an ISC — work hard, partner with your manager and be patient. I’ve seen many reps self-sabotage their leadership paths within an organization because they miss out initially on a leadership opportunity. Leadership opportunities come and go and happen when there is an intersection of organizational need and elevated personal performance or brand. Focus on what you can control, continue to develop and be patient — the rest will take care of itself.
Yieldify is an ecommerce platform taking a human-centered approach to helping brands personalize their websites. With high-profile clients like Coach and The North Face relying on the platform, the company leans on its sales leaders to ensure consistent appeal to consumer brands across the team.
Before you moved into sales leadership or management, how did you build your leadership skills as an individual sales representative?
Throughout my time as an IC the best thing I ever did was take ownership of the relationship between the SDR allocated to my territory and my work. It was a great opportunity to nurture a junior member of the staff, help mold their outlook on sales and directly benefit my pipeline as a result. I’m still close to the SDRs and BDRs I mentored and I’ve even hired them into AE roles subsequently as a VP and sales director.
You dictate the pace your career moves — for better or for worse.”
What sales skills have been most applicable for you since you moved into a leadership position?
Emotional Intelligence. This has been vital in my transition into leadership, as understanding your team is perhaps the most important trait of a good leader. Understanding their concerns, fears and feelings gives you direct insight into how to motivate them and what works for them compared to other team members.
What advice would you give to a sales rep who’s dreaming about attaining a leadership position someday?
Be the most reliable person in the team, that always delivers their number and speaks to leadership about your client conversations. Be the person that has time for those around them, celebrating their wins and mentoring them.
Don’t be afraid to be ruthless with your career. If you’re not moving at the pace you want to, move on. You dictate the pace your career moves — for better or for worse.
Finally, if you’re someone that has always worked in a large company of more than 50 reps, be open to the idea of working at a start-up, as it will help fast track your career into leadership.
