Amber Winter

Fractional CRO & GTM Advisor | Scaling B2B Companies ($1M-$10M) Through Strategic Foundation Building | Mom & Woman in Tech Advocate

Greater Madison Area

About

Hi! I'm Amber, a revenue-focused executive passionate about using technology to solve meaningful problems and helping companies build scalable go-to-market strategies. I have a proven track record of scaling B2B companies, having led an EdTech company (Web Courseworks) through significant growth and ultimately to a successful acquisition by a strategic VC partner. During that journey, I helped organizations like the American Academy of Pediatrics deliver essential continuing education to their members nationwide. What I Bring to Companies: - Strategic revenue operations and GTM strategy development - Sales process optimization and team scaling - Technology implementation for revenue efficiency - Trust-based leadership aligned with business goals I thoroughly enjoy being surrounded by passionate people, embracing technology and AI to improve business efficiency, and contributing to sustainable growth. My greatest accomplishments are my two young children, who teach me to slow down, stay curious, and find joy in everyday moments. Let's connect if you're a tech leader or CEO looking to: - Build or optimize your go-to-market strategy - Scale revenue operations efficiently - Bring your software vision to life with the right revenue foundation

Experience

  • GTM Advisor at Eneration, Inc.
    Jan 2026 - Present · 6 mos

    Helping Eneration scale their healthcare energy solutions business through: - Sales process development and CRM implementation - Discovery call frameworks and pipeline generation strategies - Training and coaching for revenue team - Conference strategy and referral program design Eneration helps healthcare systems achieve energy independence through innovative solutions, cost savings, and strategic energy planning.

  • Fractional Chief Revenue Officer (CRO) at SuiteDynamics, NetSuite Consultants & Developers
    Nov 2024 - Present · 1 yr 8 mos

    Set the GTM Foundation, contributing to 5x sustainable pipeline from baseline Optimize revenue operations to maintain team size while scaling revenue drivers Develop partnership programs w/ win-win value propositions Build product-market fit frameworks and a customer success model

  • Chief Client Officer at Forj
    Jan 2023 - Jun 2024 · 1 yr 6 mos

    After Forj and Web Courseworks merged in January 2023, I stayed on as a leader on the executive team at Forj. In my role as Chief Client Officer, I established the foundation of Client Success and managed internal client teams and external client relationships for Forj, Web Courseworks, and the subsequent acquisition of Mobilize (250+ clients). In my time in the role, our team accomplished: - Gross retention of 97% - Net retention of 107% - Increased NPS by 38 points from Spring to Fall - Supported 978,500 unique users across our products

  • Web Courseworks (6 yrs 10 mos)
    • Chief Executive Officer
      Jan 2022 - Jan 2023 · 1 yr 1 mo

      Led the business through a transformation from a custom-development, services model to a product-focused software company. This included: - Building and leading an advisory board - Hiring key executives (CRO, CTO, VP of Professional Services) - Transitioning to SaaS technology standards: Agile, Kanban, Squad Design, Product Management - Transitioning from licensing model to recurring revenue Successfully managed the sale of Web Courseworks to Forj Software (VC-backed) and transitioned to the Forj Executive Team to continue leading the business. Key Metrics from 2016 - 2022: - Revenue growth from $3.5M to $9.2M with increasing ARR - Grew EBITDA from $500K to $1.2M with increasing margins - Average Net Retention Rate of 110%

    • Executive Vice President
      Jul 2020 - Jan 2022 · 1 yr 7 mos

    • Vice President of Sales and Service
      Sep 2019 - Jul 2020 · 11 mos