Jessica Isenhower

I like figuring out how things really work.

I’ve spent most of my career somewhere between operations, enablement, data, systems, and the people expected to use them. I like the part where the neat process diagram meets reality and starts misbehaving.

I read a lot, especially strategy, psychology, systems, science fiction, and anything that gives me a new lens on a problem. I also build with AI for work and for fun. Some of it turns into useful tools. Some of it ends up in Epic AI Fails.

Coherence is the strangest example. It started as an interactive-fiction idea. Then I wanted to know how its fictional company would actually operate, so I built its annual plan, sales process, an AI skills assessment, spreadsheets, and agent blueprints. The company is fictional. The operating work is real design work.

Jessica Isenhower

What I bring to RevOps

Each line starts at the job where that work began.

WebEx
BMC
TIBCO
CSG
Litera
OfficeSpace
Customer successsince Cisco WebEx
Enablementsince Cisco WebEx
Sales & GTM opssince BMC Software
BI & datasince BMC Software
Customer success opssince TIBCO Software
Marketing opssince Litera
Applied AIsince Litera

All of it goes intoRevOps

From customer success to revenue operations.

  1. Cisco · WebEx

    2004–2012

    Enterprise CSM · Senior CS Trainer · Learning Program Manager

    Started close to the customer, which still shapes how I think about operations.

    • Built WebEx’s first structured CSM onboarding program and received the Worldwide Customer Success MVP Award.
    • Carried a Fortune 1000 enterprise portfolio and earned President’s Club for retention, adoption, and expansion performance.
    • Built a global train-the-trainer program recognized with a Cisco Innovation Award.
  2. BMC Software

    2012–2020

    Principal Knowledge Management Manager (GTM) · Manager, Sales & Technical Enablement

    Connected the sales methodology to the systems, content, and training sellers used every day.

    • Embedded value-selling and value-realization motions into Salesforce, tools, training, and deal-stage practice.
    • Led the SAVO-to-Seismic migration and increased value-based selling content utilization by 50%.
    • Built role-based onboarding, certification, learning governance, and analytics across global sellers and partners.
    • Launched mobile learning early; the work was published in Training Magazine and presented at Cornerstone’s user conference.
  3. TIBCO Software

    2020–2022

    Head of Customer Excellence Operations

    Ran customer experience operations for the Chief Customer Officer: planning, board reporting, forecasting, customer health, risk, value realization, and the leadership meeting calendar.

    • Implemented Gainsight with health scoring, automated playbooks, and risk-management processes that supported the highest subscription gross renewal rate in company history.
    • Built expansion and retention analytics used in quarterly planning and executive reporting.
    • Aligned Sales, Marketing, and Customer Success around shared customer measures and value-realization practices.
  4. Cloud Software Group

    2022–2024

    Director, Global Revenue Enablement · Director, Business Intelligence

    After a large merger: one sales motion, one set of measures, and fewer overlapping systems, without stalling 1,400+ sellers.

    • Aligned Sales, Marketing, Finance, Services, CS, and Enablement on shared processes, portfolio changes, and KPI definitions.
    • Consolidated learning platforms and related systems, delivering $1.5M in annual savings while preserving compliance and certification continuity.
    • Led BI integration, reduced dashboard duplication, and moved analytics from Tableau and Spotfire to Power BI for another $150K in annual savings.
  5. Litera

    2024–2025

    Director, Revenue Operations

    Built the RevOps function from scratch and led a team of eight covering planning, forecasting, systems, reporting, and enablement.

    • Implemented Gong from the ground up and replaced manual spreadsheet forecasting with Salesforce Collaborative Forecasting.
    • Ran end-of-month booking validation so upsell, cross-sell, and renewal ARR were recorded accurately.
    • Established the weekly, monthly, and quarterly sales cadence, and relaunched CPQ with enforced Salesforce governance.
    • Led the build of a sales dashboard that helps reps spot upsell and cross-sell opportunities and track week-over-week pipeline changes and coverage.
  6. OfficeSpace

    2025–2026

    Director, Revenue Operations

    Ran the systems and data side of RevOps, then built AI workflows on that foundation.

    • Owned the GTM systems: Salesforce, Gong, Salesloft, and Accord.
    • Led a trusted data layer as the foundation for AI workflows, including Claude access to a contract repository and full Gong transcripts.
    • Implemented a Claude pricing tool that generates pricing decks, quotes, and order forms from a library of approved legal language.
    • Designed an automated weekly sales letter and implemented the company’s first BI tool, Metabase.
  7. Series B startup

    2026–present

    First RevOps director, building the function from the ground up.

Tools, methods, and certifications

Certifications

Salesforce Certified Administrator · Salesforce Certified Agentforce Specialist · Synchronous Training Design, InSync Training

Revenue systems

Salesforce · DealHub CPQ · Gong · Gainsight · Clay · Accord

Data and reporting

Power BI · Tableau · Snowflake · Spotfire

AI and building

Claude Code · Claude Cowork · Codex · ChatGPT · MCP · n8n · GitHub · Vercel · Neon Postgres · Buffer · Recraft · Agent workflows · Web apps built with AI

Sales methods

Value Selling · MEDDPICC · Command of the Message · Value realization

Enablement and learning

Seismic · Cornerstone · Docebo · Insights Discovery

Outside of that: I live on the Texas coast, I fish, and I am entirely capable of turning a casual question into a small research project.

Jessica Isenhower deep-sea fishing
Fishing. No leadership lesson attached.