GTM Leadership
Done Differently
Helping Go-To-Market teams communicate and collaborate effectively.
I help Go-To-Market leaders …
Build self-awareness and self-leadership so they can respond with confidence instead of reacting from stress or habit.
Strengthen empathy, curiosity, and collaboration within their teams so communication improves, conflict decreases, and alignment grows.
Create healthier business systems where strong internal relationships translate into trust, connection, and sustainable growth.
About me
I’m Jill Wicklund, a former sales leader turned executive coach and teaming expert with over 20 years of experience inside go-to-market teams. I’ve sold from the inside and in the field, led sales organizations, and spent the last decade coaching and developing leaders across startups and enterprise teams.
Trusted by leading organizations, clients, and employers:
Jill is conscientious, intelligent, even-keeled, team-oriented, and has a growth mindset. She is a coach and facilitator that cares about organizations and people, and through that care and high standards, earns their respect and helps them grow their careers. I'm fortunate for having had the privilege of working with her and having her help me and my team succeed.”
Eric Sanders, SVP of Global Sales 
- Eric Sanders, Senior Vice President, Head of Global Sales“I’ve attended many leadership development programs over the years, and what stood out about working with JW LLC was the consistency in the quality of the content and the way it was brought to life through warm, engaging facilitation.
You could see the impact across our leadership team. Managers were actively coaching, using the tools in their day-to-day work, and we developed a shared language and a set of frameworks that the team continues to use.
Just as importantly, this work helped build trust and strengthen relationships across the team. It created more connection and improved cross-functional collaboration.”
- Kelly Berg, Vice President, Global Customer Experience
"Before I started working with Jill, I was struggling to find clarity in both my personal and professional life. I felt stuck in a cycle of indecision and self-doubt, unsure of how to push through the roadblocks that kept me from moving forward. My confidence was wavering, and I knew I needed guidance to get back on track.
Through our coaching sessions, Jill helped me identify the underlying issues and provided a structured approach to tackling them. She guided me in creating actionable steps that felt achievable and aligned with my goals. Jill has an incredible way of asking the right questions, which helped me shift my perspective and uncover solutions I hadn’t considered. Our work together was not only productive but also deeply insightful.
I’m incredibly grateful for the impact Jill has had on my journey, and I can’t recommend her enough."
- Charles Newport, Vice President Sales“This is not your typical stuff. It got me to levels of self-understanding that I otherwise was not able to access.” — Sales Vice President at Salesforce
“This is not your typical stuff. It got me to levels of self-understanding that I otherwise was not able to access.” — Sales Vice President at Salesforce
“I left this coaching way more confident in my sh*t” - Sales Director in Tech
“I left this coaching way more confident in my sh*t” - Sales Director in Tech
“Working with Jill challenged me in the best way. She helped me name and communicate my goals and strengths, especially in high-pressure conversations with senior leadership. She’s an empathetic guide and a sharp listener, never buzzwordy or salesy—just honest, clear, and human. I felt more grounded, confident, and prepared to take action after every session.” - Sales manager
“Working with Jill challenged me in the best way. She helped me name and communicate my goals and strengths, especially in high-pressure conversations with senior leadership. She’s an empathetic guide and a sharp listener, never buzzwordy or salesy—just honest, clear, and human. I felt more grounded, confident, and prepared to take action after every session.” - Sales manager
FAQ
-
Leaders often come to coaching when they are navigating complexity in their role. This might include:
• Managing difficult conversations
• Leading through organizational change
• Navigating team dynamics or conflict
• Developing their leadership presence
• Making important career or organizational decisions
• Strengthening how they relate to others on their team
Learn more about my experience here. -
Frameworks help leaders see situations more clearly, while reflection and practice help them notice their own patterns and responses. The combination allows leaders to apply what they learn in real conversations and decisions.
-
No, I work with many individuals outside of these roles.
-
Both. Some leaders engage coaching independently, while others are sponsored by their organizations as part of leadership development.
Please book a intro call with me to learn more.
-
Human skills are the capacities that shape how leaders relate to others and respond to situations. This includes self-awareness, awareness of others, emotional regulation, communication, and the ability to navigate complex interpersonal dynamics.