Part 1 - First Timers

Now what do I do?

I remember thinking this after I was first promoted to RVP.? My path to sales leadership began at a ~400 person VC-backed startup in the Salesforce ecosystem as a player/coach.? I learned of my promotion at our annual SKO, pulled aside by the VP of Sales and the SVP of Sales Development and Operations after a few too many pints in the early hours of the morning. ?

Being asked to step into sales leadership wasn’t a surprise - it was why I left Salesforce after almost two years to accelerate my path to a first-line leader role.? Stepping into leadership for the first time, I was hopeful for guidance on the transition and structured training, similar to when I joined as an AE.? Instead, I was thrown into the fire immediately, testing my skills, adaptability and perseverance.? A lack of dedicated leadership training and enablement tends to be common, especially at smaller, fast paced growth companies. ?

A week or two later, I was formally announced as the RVP of the SMB team? We promoted four SDRs with no prior sales experience into the SMB Account Executive role and I inherited two AE’s that had been promoted the year prior.?

And off we went!

The two experienced AEs had operated with a lot of freedom.? They were highly capable but lacked structure and a clear plan for success, instead being more reactive.? I quickly resorted to tough management and setting firm expectations, an approach I later learned was far from optimal.? The AEs tended to show up after 10am, socialize, and eat breakfast before starting work around 11am most days.? I asked them to be in the office before 9am, ready to work. ?

This caused friction and set us off on a micromanaging path.? Most days started with tension as they continued to stroll in when they wanted, impacting the entire workday. ?

As a first time leader, it is incredibly important to set the tone, communicate clear expectations, and drive accountability.? But you also need to trust and empower your people, giving them the freedom to operate as long as they’re performing at a high standard and getting the job done. ?

Looking back, here’s how I would have taken a different approach:

1. Understand Individual Work Styles: I should have invested time to better understand how each rep worked and managed their business.? I was their peer a few weeks earlier and had some insight, but not a full understanding.? Instead, I came in with an opinion instead of taking the time to dig in and verify it myself.? At the end of the day, I was MANAGING THEM instead of LEADING THEM. ? ?
2. Explain Expectations: I should have better explained why the expectations were important for the business and how I would manage the team.? Instead, I just put “9am Start” on a slide, and they viewed me as a hard-ass.? Your team may not always agree with your expectations, but if you explain the importance of the “why” behind it, the team should get behind it.? And if they don’t agree, this is also an opportunity for you to have a dialogue on ways you can optimize the business and expectations. ?
3. Share The Vision - As a new team, I needed to share the vision of what we were building and how we would get there.? When we launched, I implemented rules and expected behaviors but not a preview into the future of what we would accomplish, how we would get there and our guiding principles. No one is going to buy into rules and guidelines but they will align with a vision. ?
4. Adapt Quickly - I needed to pivot and adapt faster regarding strategy, expectations and most importantly, working with people.? The team had limited sales experience and therefore approached sales differently than I did with 10 years at CEB, Symantec and Salesforce.? This is not always a bad thing as long as you end up with the same outcome, in this case, closed won business.

Number 4 was the hardest lesson to learn because as a new leader, I felt that I had to teach them everything and be everywhere.? However, leadership is about inspiring, influencing, and empowering your team, not doing everything for them.? You need to give your people the space to learn and grow but also create a safe environment for them to make mistakes.? In my career, I’ve learned more from the losses and mistakes I’ve made along the way.? And that’s where true growth comes from.

These experiences and lessons led me to create this series “Igniting Sales Leadership,” to provide guidance and support for new leaders in similar situations.

Next up, I’ll focus on Leadership Style - What type of leader do you want to become?

"Success is not final, failure is not fatal: it is the courage to continue that counts." - Winston Churchill