Home | Coaches | Kara Gilbert

“Kara is a dynamic and extraordinarily talented coach who is able to drive change while bringing others along on the journey. She brings out the best in others through her passion and commitment to development. I had the great pleasure of working with and learning from Kara.”

Corey Thomas - CEO, Rapid7

Kara Gilbert

Executive Coach

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Kara Gilbert is an executive coach with a passion for people, excellence and for supporting leaders to thrive in rapidly changing environments. As a coach and transformative leader with 20 years of experience in Fortune 500 companies and high-growth startups, Kara is laser-focused on you and aligning your values with your professional and personal goals. Executives that have worked with Kara appreciate her warmth, clear insights, and direct actionable feedback. Kara creates an atmosphere of trust – a non-judgmental listening space – from which breakthrough strategies and new insights arise. She coaches high-performing and high-potential executives to leverage their innate strengths through systems and teams to achieve consistent, next-level results – personally and professionally.

Kara is an entrepreneur and risk-taker who is known for empathetic yet honest communication, and the skills to go from boardroom to frontline with an eye on key objectives and strategy. She has pivoted herself from sales and customer success to focus on people and talent strategies to fuel growth during times of unprecedented change. Clients appreciate Kara’s ability to evaluate options, understand customers, and activate people. Kara coaches with a bold vision for the future.

If not with her husband and kids, Kara is likely on her Peloton, at yoga class, reading or volunteering. Kara enjoys travel, baking, games and any Boston sporting event.

“Kara is a perfect combination of strategic visionary, student of human behavior and all-around caring person. Kara has the ability to take in information and provide guidance and counsel that rivals the best management professionals and coaches working today."

Eric Swidey - VP of Talent Acquisition, Turbonomic

Break Through Business Results

As an accomplished senior executive herself, Kara is valued as a strategic listening partner – empowering leaders to tackle their personal and professional agendas with consciousness and confidence.

  • Coached CEO and CRO to enable 80-person sales organization during rapid change in forecasts, best practices and systems. The company went public after 3 years of consistent and unprecedented growth.
  • Coached sales leaders of a global technology company to increase accountability and unleash new energy resulting in retention of high potentials and 50% growth in the business.
  • Coached sales Vice President to re-prioritize and successfully enable work/life integration including family dinners and coaching a sports team while simultaneously exceeding professional goals.
  • Mentored the founders of a SaaS startup company during rapid growth to triple ARR while maintaining culture and core values.
  • Coached business leaders at a high-growth software company to elevate talent strategy enabling rapid hiring and doubling the company size in 12 months.
  • Coached sales leaders to grow a new SMB market 100% year-over-year through talent acquisition, team alignment and account segmentation.
  • Coached business leaders on presentation content and style for first-time Board level review and discussion.

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Professional Expertise
  • Executive Coaching
  • Complex Matrix Organizations
  • Leadership Development
  • Multi-Channel Sales/GTM
  • Sales Development & Leadership
  • Talent Strategy + Acquisition
  • Venture Capital
Select Industry Expertise
  • Cloud Services/SaaS
  • Enterprise Software/Technology
  • Financial Services
  • Healthcare
  • Information Security
  • Professional Services
  • Strategy
Education/Certifications
  • BA International Relations – American University
  • Break Through Consulting Business Results Coaching Certification
Positions Held
  • Executive Coach - Break Through Consulting
  • Limited Partner – Stage Two Capital
  • Chief People Officer – Turbonomic
  • Operating Partner – Bain Capital
  • Senior Vice President, Sales – Rapid7
  • VP, OracleDirect – Oracle Corporation

"Merry was brilliant in never judging, always advocating. This allowed me to open up more in my dialog with her. It’s a technique I am now working to implement with my own team"

Casey Wells - Managing Director, Accenture

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