Client Success Story: Elevating Executive Leadership Through Coaching

How Executive Coaching Transformed Leadership, Influence, and Trust

When Ali Mapes, Senior Vice President of Customer Success at Ordergroove, first engaged in executive coaching with StartWise, she sought to refine her leadership approach, strengthen executive team collaboration, and build deeper trust within her organization. What she discovered was not just professional growth—but a powerful personal transformation.

The Challenge: Navigating Leadership in a High-Stakes Environment

As a seasoned executive, Ali had already built a successful career leading customer success teams. However, stepping into a new leadership role at Ordergroove brought fresh challenges. While she had a strong foundation in operational efficiency and team management, she was stepping into the e-commerce industry for the first time.

Ali recognized the need for deeper trust-building with her executive peers, more strategic conversations, and a leadership approach that balanced directness with influence. She also wanted to proactively shape her personal brand within the organization.

“For me, executive coaching has led me to more in-depth conversations that I wasn’t able to have with other people on my executive team. I needed coaching and guidance on how to approach certain situations or work with certain personalities to get to the outcomes that were important for me.”

The Solution: A Thoughtful, Strategic, and Personalized Coaching Approach

Ali partnered with Sara Gupta, founder of StartWise, whose unique coaching approach blends executive-level experience with outcome-driven leadership development.

From their very first session, Sara provided Ali with tools to:

• Navigate High-Stakes Conversations – Coaching helped Ali step back and see situations from multiple perspectives, leading to more effective discussions with executives, board members, and customers.
• Strengthen Executive Presence – Through targeted coaching, Ali gained clarity on how to build influence and trust, rather than just driving toward outcomes.
• Develop a Proactive Leadership Mindset – Rather than reacting to challenges, Ali learned to anticipate obstacles, refine her strategy, and lead with confidence.
• Prioritize Personal Growth – While the initial focus was on leadership effectiveness, coaching also helped Ali invest in herself, rethinking how she wanted to grow her career beyond her current role.

“I thought I needed coaching to improve my approach with my executive team and customers. But what I really found was an investment in myself—and I didn’t realize how much I needed that.”

The Results: A Leadership Shift That Transformed the Organization

After six months of coaching, Ali saw a significant transformation in both her leadership style and her organization:

• Greater Executive Team Trust: Ali’s approach to trust-building created more openness and vulnerability in leadership discussions, strengthening executive alignment.
• Stronger Influence & Brand: Coaching helped Ali refine how she positioned herself internally, ensuring her strategic insights were heard and valued.
• More Effective Stakeholder Management: Ali learned to engage multiple stakeholders proactively, building buy-in before key decisions were made.
• Personal Growth & Reflection: Coaching provided a space for Ali to prioritize her own development, something she hadn’t done before.

“The trust I’ve built with my executive team has changed the way we work together. The conversations we are having now are deeper, more thoughtful, and more productive.”

Why Coaching Works: Lessons from Ali’s Experience

Ali’s story is a powerful example of why executive coaching isn’t just about leadership tactics—it’s about transformation. Through coaching, she not only strengthened her leadership impact but also deepened her self-trust, improved her executive relationships, and found clarity in her long-term career growth.

For executives navigating high-pressure roles, coaching offers more than professional guidance—it creates a foundation for strategic thinking, influence, and long-term success.

“It’s so important to find the right coach – someone who truly cares about your journey. From day one, I knew Sara had the experience and insight to help me grow.”

Are You Ready for Your Leadership Breakthrough?

If you’re a senior leader looking to elevate your impact, build trust, and strengthen your executive presence, StartWise can help. Book a consultation today to explore how coaching can unlock your full leadership potential.➡️ Schedule a Consultation