Revenue Operations & GTM Strategy

Cassandra
Hitchcock

Building the infrastructure of growth

The Swiss Army knife of revenue leadership. I've spent 20 years operating as the connective tissue between C-suite vision and field execution, equal parts strategist, operator and trusted advisor. Where others see silos, I build systems. Where teams stall, I create momentum. If you need someone with eyes and ears across the org who can translate the boardroom into action on the ground, that's exactly what I do.

View experience
20+
Years in B2B SaaS
$100M+
Org Scale
3×
President's Club
GTM
Strategy & Execution

Where strategy meets the field

I bridge the gap between high-level GTM strategy and tactical field execution. My work lives at the intersection of people, process and technology, creating systems that allow revenue teams to operate at their best without burning out.

I believe operational rigor and emotional intelligence are not mutually exclusive. They're the twin engines of sustainable growth. The most effective organizations I've built and worked within treat both as first-class priorities.

Based in Chicago. Open to executive opportunities in Revenue Operations, Sales Enablement and GTM leadership, remote or hybrid.

Revenue Strategy

Aligning Sales, Marketing and Customer Success to a single revenue roadmap that everyone can execute against.

Enablement

Reducing ramp time and increasing quota attainment through systematic coaching frameworks and scalable programs.

Change Management

Navigating complex pivots, new product feedback, rollouts and high-growth scaling with clarity and minimal organizational friction.

Experience

A track record built across SaaS, hospitality tech, automotive and digital media.

2025 – Present
Main St Mercantile · Lafayette, IN
Business Transition & Sales Strategy Lead
Consultative

Brought in to modernize a 40-year legacy brand facing an existential pivot. Liquidated high-value retail inventory, decommissioned the physical footprint for commercial leasing, and built the e-commerce infrastructure to carry four decades of market equity into a fully digital future.

Consulting GTM Strategy Business Transitions E-commerce
2023 – 2025
Inuvo · San Jose, CA
Senior Director, Client Success & Revenue Operations
Remote

Drove the organizational realignment that delivered the highest quarterly revenue in company history. Built workflows that sustained a 90% customer retention rate while opening new expansion and referral channels, and designed the executive reporting frameworks that gave leadership clear visibility into enterprise growth opportunities.

RevOps Client Success AI / AdTech
2021 – 2023
SevenRooms · New York, NY
Director, GTM Enablement
Remote

Built "7RU," SevenRooms' internal company university, cutting new-hire ramp time from 6 months to 4 through automated certifications and e-learning. Refined contracting and upsell processes that drove a 25% ARR increase and 30% lift in product upsells, while leading the GTM roadmap for a fully remote global org across Sales, Implementation and Success.

Sales Enablement Hospitality Tech High-Growth Scaling
2019 – 2021
ChowNow · Los Angeles, CA
Sr. Manager, Sales Enablement
Remote

Transformed a fragmented onboarding process into a fully automated training ecosystem, cutting time-to-first-sale from 42 days to 16. Launched the "Value Pitch Certification" and a weekly market trend video series that modernized how reps showed up in front of clients, earning a 75% average open rate.

Sales Enablement Onboarding Restaurant Tech
2006 – 2019
Cars.com · Chicago, IL
Progressive Leadership Roles · 12.5 Years
Customer Success / Sales Management / Revenue Operations / Product Marketing and Sales Enablement

A career-defining tenure that shaped every dimension of my leadership approach. Authored and trademarked "The Four P's of Automotive Marketing™," built and coached a 30+ person sales team to exceed targets by 32%, retained $1.3M in at-risk revenue through a standardized save process, and generated over $1.2M in incremental revenue through market-level planning. Three-time President's Club winner. Recognized in the Top 10% of Sales Leadership nationally.

Product Marketing Sales Leadership Customer Success President's Club x3

Core skills

The capabilities I bring to every engagement, from the 30,000-foot strategy to the day-to-day execution.

Revenue Operations
GTM strategy & roadmapping
Sales forecasting & reporting
CRM architecture & adoption
Pipeline management
Revenue infrastructure design
Sales Enablement
Sales ramp & onboarding
Coaching frameworks
Playbook development
Quota attainment programs
ValueSelling & Challenger Sales methodology
Leadership & Culture
High-EQ leadership
Organizational change management
Cross-functional alignment
High-performance team building
Stakeholder management
Strategy & Growth
B2B SaaS scaling
Product & market strategy
Client success & retention
Business transitions
Relationship-led growth
Challenger Sales Certified
Leadership Foundations
Sales Coaching Certified
Sales Operations
Leading with Emotional Intelligence
Purdue University, BS Retail Management

Outside the office

The things that keep me curious, grounded and creative.

Photography

I'm drawn to the art of capturing a moment: light, texture, stillness. Photography taught me how to slow down and really see what's in front of me, a habit that's made me a better observer in every room I walk into.

Travel

New places, new perspectives. Travel is my reset button and one of the best professional development tools I've found. Navigating unfamiliar cultures and contexts sharpens adaptability, empathy and the ability to read a room.

Rescue Dogs

Fostering and adopting rescue dogs is one of my greatest joys. There's something profound about giving an animal a second chance, and watching them trust again. My house has always had multiple rescue dogs in it, and I wouldn't have it any other way.

Design

I've always had an eye for design: how things look, how they feel, how they communicate without words. That same instinct extends to how spaces are organized. Everything should have a place, and when it does, the whole system just works better. Dabbling in design and organization keeps my creative instincts sharp and reminds me that great experiences, in products and in teams, are always intentional.

Sports

Lifelong Purdue Boilermaker Basketball fan and a devoted Cubs faithful who considers a day at Wrigley Field one of life's great pleasures. Whether it's cheering on the black and gold or soaking in the ivy and the sunshine on the North Side, rooting for my teams is non-negotiable.

Let's build something

"Repeatable revenue, reduced friction and high-performance cultures."

Whether you're scaling a revenue org, navigating a complex pivot, or looking to build an enablement function from scratch. I'd love to connect.

Open to executive roles in Revenue Operations, GTM Enablement and Sales Strategy. Also available for consulting engagements.