Jeremy Painkin is a game-changing leader who thrives on turning challenges into triumphs. As Chief Revenue Officer at Naylor Association Solutions, he’s not just driving revenue—he’s reshaping the playbook for success. With a knack for inspiring teams and a strategic mind wired for growth, Jeremy consistently delivers extraordinary results.

Jeremy has a proven track record of transforming underperforming organizations into top-tier performers. In one of his standout achievements, he led a division from last place to the #1 spot, crushing sales quotas by 338%. He’s built and led teams of 58 Account Executives, driving $1M in new monthly revenue and increasing the client base by 15% to over 7,500. His expertise lies in crafting strategies that work and empowering people to execute them flawlessly.

What sets Jeremy apart is his leadership style. He’s a builder of trust, a champion of transparency, and a mentor who invests in his team’s growth. Jeremy knows that great leaders create great cultures, and he’s passionate about making workplaces where people thrive.

His career includes senior roles at Community Brands, Cascade, and Gartner, where he mastered go-to-market strategies, data-driven decision-making, and client success. But Jeremy doesn’t stop at business. He’s an Executive Board Member for The Leukemia & Lymphoma Society and a coach for Alzheimer’s initiatives, living his commitment to community impact.

Jeremy Painkin isn’t just a leader—he’s a catalyst for transformation, a mentor to many, and a force for good in every role he takes on.

What motivates you when things get tough?

When things get tough, I’m motivated by the people I lead and the responsibility I have to them. Knowing that my actions can make a difference for my team, clients, and company drives me to push forward. I also find strength in my long-term vision; remembering why I started helps me weather short-term challenges. On a personal level, my family’s support and belief in me provide a grounding force. Lastly, I thrive on the challenge itself—tough times are opportunities to learn, grow, and prove that success is always within reach with the right mindset.

Tell us 3 surprisingly easy and 3 surprisingly difficult things about your business.

Surprisingly Easy:

Building Trust with Clients: Genuine communication and delivering on promises make trust-building straightforward. People appreciate honesty.

Identifying Growth Opportunities: Data-driven insights and client feedback often highlight opportunities quickly. The key is acting on them.

Fostering Team Spirit: A shared vision and open recognition of achievements naturally unite people.

Surprisingly Difficult:

Balancing Long-Term and Short-Term Goals: Prioritizing immediate wins without losing sight of the bigger picture is always tricky.

Navigating Market Shifts: Even with preparation, external factors like economic changes require constant adaptation.

Scaling Without Compromising Culture: Rapid growth can strain the very values that make a team thrive, demanding extra attention.

 

The Role of Coaching in Sales Leadership: Developing Future Stars and Driving Long-Term Success

 

What are the 3 things you like the least about your work and why?

Red Tape: Bureaucracy can slow innovation, which is frustrating when you’re eager to act on a good idea.

Missed Opportunities: Seeing potential deals fall through, often due to factors outside our control, can be discouraging.

Work-Life Balance Challenges: Leading large teams and organizations requires long hours, sometimes at the expense of personal time. However, I work on managing this by delegating effectively and setting boundaries.

What do you think are your 3 biggest weaknesses and how are you overcoming them?

Impatience: I often want results yesterday. To overcome this, I’ve learned to celebrate small wins and trust in long-term strategies.

Delegation: Early in my career, I felt the need to do everything myself. I’ve since realized the value of empowering my team and trust them to deliver.

Overanalyzing: I sometimes overthink decisions. To combat this, I use frameworks and trust my instincts when necessary.

Tell us about a time you were dead wrong about something.

I once underestimated the impact of a market shift on one of our key revenue streams. I initially thought our team could ride it out without significant changes, but results proved otherwise. I admitted my mistake, regrouped with the team, and adapted our strategy to realign with market needs. It was humbling but reinforced the importance of listening to data and being willing to pivot quickly.

What is the biggest challenge you face each day and how do you handle it?

Balancing competing priorities is my biggest challenge. Every day brings new opportunities and demands, each seemingly urgent. I handle this by staying disciplined with my time, setting clear priorities, and ensuring my focus aligns with long-term goals. I also empower my team to make decisions, trusting them to manage what they can without waiting for my input.

What do you value most and why?

I value trust the most. Without it, teams can’t collaborate effectively, clients won’t stick around, and long-term relationships are impossible. Trust is the foundation of every success I’ve had in my career. It’s built through transparency, consistent actions, and delivering on promises. When trust exists, everything else—teamwork, innovation, growth—becomes much easier.

What are you doing that is difficult? Please explain.

Scaling a business while maintaining a cohesive culture is incredibly challenging. Rapid growth often brings pressure to compromise values or prioritize speed over quality. I’m addressing this by investing in leadership development, clearly communicating our values, and being intentional about hiring individuals who align with our mission. It’s not easy, but it’s worth the effort.

Who is your favorite motivational speaker and why?

Simon Sinek is one of my favorite motivational speakers. His focus on purpose and starting with “why” resonates deeply with me. His insights into leadership and building trust align with my own approach to leading teams. I appreciate how he simplifies complex ideas, making them actionable and relatable. His philosophy inspires me to stay focused on what truly matters.

What advice would you give to your younger self and why?

I’d tell my younger self to focus on building relationships and not stress about having all the answers immediately. Success is a marathon, not a sprint, and the people you surround yourself with are more important than any single accomplishment. I’d also encourage myself to take more calculated risks earlier—they’re often where the biggest growth happens.

Are you willing to be a mentor? If yes, what is the best way to reach you?

Absolutely, I love mentoring others. It’s fulfilling to share my experiences and help others navigate their challenges. The best way to reach me is through LinkedIn. I’m always open to meaningful conversations with those eager to grow.

Just for fun, what is your favorite ice cream flavor?

Cookies and cream, hands down. It’s the perfect mix of creamy and crunchy, and it always reminds me of carefree childhood summers. It’s a simple indulgence that feels like a reward after a long day. Plus, it’s versatile enough to pair with almost any dessert!

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