Principal
Cassandra Freeman
Revenue and go-to-market executive with 12+ years building and scaling B2B and SaaS organizations across SMB, mid-market and enterprise. Cassandra’s experience spans sales leadership, GTM strategy, revenue operations, partnerships, conversion and demand, including leading the largest sales vertical of a healthcare technology company through its NYSE IPO.
Areas of expertise
What Cassandra solves for a business.
Revenue leadership
GTM
Partnerships
Revenue operations
Brand & demand
Selected results
Measurable outcomes.
$19M ARR delivered during IPO-scale growth
20% year-over-year growth
8 consecutive quarters above 120% of plan
50-person sales organization led through public-market growth
Partner ecosystem scaled from 7 to 40+, driving $3M+ in partner revenue in twelve months
33% reduction in sales cycle
Method
Sales operating system
Weekly forecast and pipeline inspection cadence with clear exit criteria
Deal reviews for late-stage and top deals
Hiring profile and onboarding plan
Enablement rhythm covering messaging, discovery and objection handling
Manager scorecards and performance standards
Cross-functional alignment to tighten funnel handoffs
NYSE IPO experience
Public-market growth requires operating discipline long before the listing day.
Cassandra led the largest sales vertical of a healthcare technology company through its NYSE IPO, managing 20 Account Executives and 30 SDRs while maintaining eight consecutive quarters above 120% of plan.
- $19M ARR delivered during IPO-scale growth
- 20% year-over-year growth
- 8 consecutive quarters above 120% of plan
- 50-person sales organization
Prior operating experience
Where the experience was built.
- Senior sales leadership at a publicly traded healthcare technology company.
- Corporate development leadership at a growth-stage healthcare SaaS platform.
- Executive revenue leadership at a venture-backed technology company.
- Leadership across high-velocity SMB, mid-market and enterprise sales motions.
- Technology, referral and integration partnerships across healthcare and vertical SaaS ecosystems.
Enterprise partnerships
Commercial partnerships at scale.
Enterprise partnership experience spanning global technology platforms, Fortune 500 brands, national retailers and healthcare technology companies.
Cassandra has negotiated and launched partnerships across technology, healthcare, retail and consumer sectors, including referral, channel, integration, co-selling and commercial partnership models.
Brand & creator experience
Firsthand experience with modern customer acquisition.
In addition to her operating background, Cassandra has built an audience and developed content across beauty, wellness, lifestyle and consumer categories, providing firsthand experience with modern customer acquisition, social content, UGC and creator-led demand.
That work includes building an audience from zero to 18,000 followers and more than 5 million views, and running paid and gifted campaigns for beauty, skincare and fashion brands. It supports her Brand & Demand work rather than defining it.
- Brand positioning, offer design and messaging
- Content and social strategy built around search discovery
- Creator and UGC programs: sourcing, briefing, whitelisting and paid amplification
- The path from content to booked appointment or closed deal
- Measurement tied to acquisition, conversion and revenue, not vanity metrics
Speaking & industry leadership
Bringing operating experience into the room.
CJM principals bring their operating experience to leadership discussions, panels, workshops, company trainings and industry events across revenue growth, sales leadership, franchising, brand development and business operations.
Speaking & workshop inquiriesPerspectives from people we’ve worked with
Cassandra is the rare leader who makes everyone around her better, as evident in her top performing teams. No leader has equipped me better to succeed as both a top-performing rep and a sales leader. Lofty goals felt attainable, hard work was fun, and challenge was celebrated. To this day, she is a mentor I trust.
Need a revenue organization that forecasts accurately, converts consistently and scales beyond a few strong performers?
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