From Rep to Leader: Lessons on Sales Leadership and Confidence

The move from individual contributor to sales leader is one of the hardest transitions in a sales career. In this episode of the Revenue Revolution podcast, Ciara Flit explains what really changes when you step into leadership and what she wishes she had known sooner.

Why most sales careers start by accident

Ciara did not plan a career in tech sales. She studied food science in Dublin and only discovered sales through a LinkedIn message advertising free lunch.

Her early roles as a BDR and AE helped her realize that sales rewards curiosity, resilience, and learning by doing more than perfect preparation.

How sports shape stronger sales leaders

Years of competitive basketball taught Ciara how to handle pressure, setbacks, and teamwork.

She credits sport with building resilience, competitiveness, and the ability to support teammates through both wins and losses.

Why managing people is harder than closing deals

Leading a team is more complex than managing your own pipeline.

The hardest shift was learning to step back, trust reps to make mistakes, and resist jumping into calls with the answer.

"Helping them fail early is far better than doing it for them."

How to transition from peer to manager

The move from peer to manager came with discomfort.

Ciara learned that leadership is not about being liked. It is about being respected and consistent.

She also stressed the importance of treating top performers and struggling reps with the same level of care and attention.

What to do when joining a team as an external leader

Joining a new company as a manager brings a different challenge.

Ciara focused on listening first. She spent time understanding each rep’s motivation, how they like feedback, and who the informal leaders were on the team.

Before major changes, she spoke with influential reps in advance to gain alignment and avoid surprises.

Why over-communication is a leadership superpower

The skill Ciara most wishes she had earlier was over-communication.

As an individual contributor, independence worked. As a leader, silence created risk.

Clear, frequent updates upward and downward helped build trust and prevented issues from escalating.

How sales leadership has changed with the market

Earlier in her career, growth was the only focus.

Today, buyers are cautious. Decisions involve more stakeholders and longer evaluations. Sellers must prove value, efficiency, and time to impact, not just features.

How leaders can help more women move into sales roles

Representation matters.

Seeing women in leadership and sales roles makes others more likely to apply. Leaders should actively call on women in discussions, encourage their input, and be vocal advocates.

Education also matters. Many young women still do not know tech sales is a career option.

The moment that captures why sales teams matter

One late night waiting for a major deal to close stands out.

When the signed contract came through, the entire team celebrated like they had won a championship. That shared moment of effort, tension, and success is why many people stay in sales.

Sales leadership is challenging, emotional, and demanding. But when done with trust, empathy, and clear communication, it creates moments that last far beyond the numbers.