Client Success Story: Rebuilding Confidence and Clarity in Leadership
How One SaaS Executive Found Clarity, Confidence, and Control During a Career Inflection Point
When Jessica Reser Osborn returned from maternity leave, she expected a challenging transition. What she didn’t anticipate was the emotional toll of stepping back into a fast-moving organization that had changed drastically during her absence. As a seasoned customer success executive in the SaaS industry, she wasn’t new to pressure—but this time felt different.
Instead of support, she encountered organizational politics, shifts in leadership, and subtle but painful erosion of the trust she had built prior to her leave. Like many women in similar positions, she faced what she described as the equivalent of starting a new job while feeling more vulnerable than ever before.
The Challenge: A Return to Work That Felt Like Starting Over
Jessica’s return to work came with:
- A new leadership structure and shifting political dynamics
- A sense of being overlooked and underestimated despite a proven track record
- An environment that felt chaotic, fast-paced, and emotionally draining
Amid these challenges, she found herself questioning whether this was still the right place—and what kind of leader she wanted to be going forward.
“It was almost like starting a new job. The team dynamics had shifted, and the trust I had built felt forgotten. I was trying to reestablish myself while still finding my footing again as a new mom. It was a lot.”
The Coaching Solution: Building Clarity and Self-Trust
Jessica turned to coaching as a way to find clarity and build a new leadership foundation. Through her work with StartWise, she engaged in a process designed not only to reorient her professionally, but to reconnect with her personal purpose and values.
Using the StartW.I.S.E. Method, Jessica and Sara focused on:
Why – Rediscovering Purpose
Together, they explored what truly gave Jessica meaning—not just at work, but in life. Through a life purpose quadrant exercise, Jessica zoomed out beyond the day-to-day stressors to reflect on her values, goals, and identity.
“That zoom out was everything. I was so deep in the weeds that I’d lost sight of what mattered to me. Gaining that perspective helped me ground myself again.”
Intuition – Reclaiming Confidence
With clarity came self-trust. Coaching gave Jessica space to reflect, reset, and choose how she wanted to respond to the pressures around her rather than react to them.
*”You shared a quote with me—’Between stimulus and response is where we have choice.’ I pinned it to my desk. It became my anchor in the chaos.”
Strategy – Creating a Leadership Roadmap
Rather than react to the political changes and new leadership dynamics, Jessica began building a strategy that was authentic to her strengths and values. She set goals for how she wanted to show up and lead, regardless of the noise around her.
Execution – Taking Back Control
Through accountability and ongoing support, Jessica began to navigate her return with more confidence and intention. She no longer felt like she was being swept up in the chaos—she was building her own path forward.
“Coaching gave me the tools to find my footing and my voice again. It was one of the most powerful investments I’ve made in my career.”
Why This Matters
Jessica’s story is a powerful reminder that even the most experienced leaders can find themselves feeling disoriented or stuck after a major transition. Whether it’s a new role, a return from leave, or a toxic team dynamic, no one should have to navigate it alone.
Coaching provides:
- Perspective during uncertain times
- Practical tools for regaining confidence and influence
- A safe space to reflect, recalibrate, and lead with intention
“Sara’s approach is thoughtful, intentional, and grounded. She brings authenticity and deep understanding because she’s been there—she knows what these roles are really like.”
Ready to Lead With Clarity and Confidence?
If you’re in a moment of professional transition—whether you’re stepping into a new role, returning from leave, or navigating complex leadership dynamics—StartWise can help.
📅 Book a consultation to explore how coaching can help you reclaim your confidence, define your strategy, and lead with impact.