Head of Operations
About the job
- Experience scaling a chaotic $5M–$25M annual recurring revenue software-as-a-service business.
- Experience cleaning up messy customer relationship management systems.
- Experience improving forecast discipline and reducing churn in usage-based software-as-a-service businesses.
- Experience installing operating discipline in scrappy teams.
- Experience working directly with a driven founder.
- Ability to operate calmly under pressure and challenge a chief executive officer.
- Strong numerical and revenue orientation.
- Own forecast accuracy to within plus or minus 10 percent.
- Own pipeline discipline, net revenue retention, gross churn reduction, enterprise expansion, and revenue visibility across the organization.
- Run sales, marketing, customer support, and engineering.
- Build a clean forecasting system and clear customer segmentation within the first 90 days.
- Run revenue meetings and remove the founder from operational noise.
- Make revenue predictable, establish a repeatable enterprise motion, stabilize net revenue retention, and tighten internal execution.
- Install revenue leadership and scale the company toward eight-figure revenue.
- Build infrastructure-level positioning in Media and Publishing.
About the company
Summary of Cache Ventures 1) What they do: Cache Ventures is a venture equity firm that builds, advises, and invests in software and tech-enabled services companies at all growth stages, aiming for long-term value through deep founder partnerships. 2) How their product works: They combine capital with strategic guidance and hands-on support to help founders grow, expand their networks, and execute plans clearly, working closely with teams to reach ambitious goals. 3) How they differ from competitors: They emphasize long-term, founder-centered partnerships and use a mix of funding, strategic advice, and active involvement across the growth spectrum, rather than just providing capital. 4) Their goal: To help teams create enduring, scalable companies by delivering resources and close collaboration that accelerates growth and outcomes.
Company Size
11-50
Company Stage
N/A
Total Funding
N/A
Headquarters
New York City, New York
Founded
2013
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Simplify's Take
What believers are saying
- The website updated August 24, 2026, signals active branding and ongoing firm maintenance.
- LinkedIn shows 2026 headcount growth to 11-50 employees, suggesting broader operating capacity.
- Cache’s indefinite-horizon strategy fits distressed or overlooked software assets needing operational turnaround.
What critics are saying
- Cache has minimal public transparency; 2026 disclosures reveal no fresh deal pipeline or KPIs.
- Old acquisitions like LeadOwl and TheChecker create concentration risk if legacy software churns.
- If the studio stops sourcing proprietary deals, Cache becomes a tiny, undifferentiated micro-fund.
What makes Cache Ventures unique
- Founded 2013 by Sean Heilweil and Jarrett Lusso; Cache blends studio, advisory, and investing.
- Cache Ventures still positions itself as builders of SaaS, not just passive capital providers.
- Its portfolio approach spans acquisitions like LeadOwl and TheChecker, emphasizing hands-on operational control.
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Benefits
Health Insurance
Dental Insurance
Vision Insurance
Remote Work Options
Flexible Work Hours
Company Equity
Parental Leave
Wellness Program
Mental Health Support
Home Office Stipend
Conference Attendance Budget
Professional Development Budget
Company News
We build, advise, and invest in businesses that fill industry gaps, pioneer new markets, and challenge the old way of doing things.