Your Entrepreneur Era: Take Your First Steps

About the role

Connect 1-on-1 with vetted Experts to navigate leadership, starting your own business, finding work after 50, and more. Whether you’re deep in your career, navigating a complex path, or managing a transition, Sam provides advice and actionable support to ensure you are prepared and in control.

Career and Leadership Experts are professionally trained, deeply knowledgeable, and heavily vetted to advise women on a wide range of areas, including:

• Career transitions
• Building your own business
• Building a personal brand
• Balancing work & caregiving
• Leadership coaching

How it works

• Choose Your Focus Area: Select the life transition you’re navigating—whether it’s eldercare, a high-stakes career pivot, relationships, or grief.
• Meet Your Expert: Browse our hand-selected roster of the top 1% of vetted specialists. Read their backgrounds and find the professional whose lived experience aligns with your specific hurdle.
• Book a Targeted Session: Pick a specific, 60-minute session tailored to your exact needs. Pay per session starting at $50—with absolutely zero subscriptions, packages, or long-term commitments. Sessions are 60 minutes or less.

Guaranteed outputs and next steps, every time. Not sure what you might need? Book a complimentary 15-minute Navigator call for additional personalization.

Featured Experts

Real women, professionally certified and trained, with lived experience. All Experts have 15+ years of experience.

• Entrepreneurship: Akua Okunseinde, MBA

  Akua is a former Google and American Express corporate ladder-climber. She holds real-life business experience as the co-founder of the skincare brand Karité. She has an MBA from Columbia University and a BA from Tufts University.

• Building Confidence: Joanna Lovering

  Joanna’s approach blends psychology, strategy, and style to support women in leading with confidence and authenticity—because the workplace doesn’t need more perfect people, it needs more real, self-led women who know their worth and aren’t afraid to own it.

• Work after 50: Mary Despe de Echemendia

  Mary has more than 15 years of coaching experience guiding professionals, especially women over 40 through promotions, new roles and career transitions. She has an MBA from Holt International Business School and a BA from the University of Illinois.

Featured Support Sessions

Support Sessions are private, 1-hour or less sessions with real human experts (no AI here) that include follow-up and customized action plans to guide you in your journey.

• Your Entrepreneur Era: Take Your First Steps – Bring that idea to life with a Sam Expert. Leave with a plan for what comes next and been seen in this new era.
• Career Contingency: A Pre-Layoff Plan – Are you concerned about the stability of your current role? Talk it through with a Sam Expert and brainstorm ways to be prepared.
• Executive Presence: Power and Poise – New to leadership? Or just want to level-up? This session offers personalized support to bring that leader in you — out.
• Career Crossroads: Make Your Move – Stay or go? Discuss and workshop your options in this private session with a Sam career Expert.

Pay

Sessions start at $50 per 60-minute session. No subscriptions, packages, or long-term commitments required.