GTM Leadership
Done Differently

Helping Go-To-Market teams communicate and collaborate effectively.

  • Have you ever pushed hard for results, only to feel the connection and trust within your team start to slip?

    How I can help

  • Have you ever achieved your revenue goals, but done it at the cost of your own peace and energy?

    How I can help

  • Have you ever struggled to retain talent or hit your revenue targets, but could not quite pinpoint why?

    How I can help

  • Have you ever coached other leaders, only to realize no one’s really coaching you?

    How I can help

  • Have you ever hit your revenue targets, but only by stepping in like a super rep yourself — doing both your job and your teams?

    How I can help

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.

Here's how

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.

Learn more

What people say

“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 leader from Austin, TX

“I left this coaching way more confident in my sh*t” - Sales leader from Austin, TX

“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.” - revenue leader, partner team at Salesforce

“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.” - revenue leader, partner team at Salesforce

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.