[Hiring] Chief Revenue Officer @Flosum

Role Description

We are a bootstrapped, profitable enterprise SaaS company at $30M ARR with a clear trajectory to $100M. We have built the only 100% natively-architected platform in our ecosystem for DevSecOps, Data Protection, and Security—serving Fortune 500 enterprises across regulated industries including financial services, healthcare, government, and hospitality.

We are not looking for a CRO who will spend six months “assessing the landscape.” We need a proven operator who has personally scaled a SaaS business from $20–40M to $100M+ ARR, who understands that profitable growth is non-negotiable, and who can build and execute a revenue engine that compounds quarter over quarter.

Core Responsibilities

• Revenue Strategy & Execution
  • Own the full revenue number: new business, expansion, renewal, and retention across all segments (Enterprise, Mid-Market, and emerging PLG).
  • Design and execute the go-to-market strategy to scale from $30M to $100M ARR within 3–4 years while maintaining profitability.
  • Build and operationalize a quarterly planning cadence with bottoms-up forecasting, pipeline coverage models, and segment-level unit economics tracking.
  • Establish minimum deal size thresholds and systematically prune low-value accounts that dilute team capacity and drag down margins.
  • Drive cross-sell and upsell motions across the five-product portfolio, increasing average contract value and multi-product adoption rates.
• Pipeline & Demand Generation
  • Build a scalable, multi-channel demand generation engine spanning outbound prospecting, content marketing, digital campaigns, events, partner referrals, and product-led growth.
  • Own pipeline coverage ratios and ensure 3–4x pipeline-to-quota coverage at all times across segments.
  • Implement rigorous pipeline inspection and deal management processes with weekly forecasting reviews, stage-gate criteria, and data-driven coaching.
  • Personally engage in strategic pipeline development for enterprise accounts, including executive-to-executive relationship building.
• Product-Led Growth & Innovation
  • Design and execute a PLG motion that creates a self-service entry point into the platform, converting free or low-cost users into enterprise contracts.
  • Build the instrumentation, analytics, and product-sales handoff processes required to identify and convert PLG-qualified leads into sales-assisted opportunities.
  • Develop innovative go-to-market strategies that differentiate the company from competitors relying on traditional sales motions, including community-led growth and ecosystem-based strategies.
• Enterprise Sales & Large Deal Execution
  • Personally lead and close strategic enterprise deals with Fortune 500 accounts, particularly in regulated industries with complex procurement and compliance requirements.
  • Penetrate large enterprise accounts through multi-threaded relationships, executive sponsorship, and value-based selling that ties platform outcomes to business-critical KPIs.
  • Build and manage a structured enterprise deal process including discovery frameworks, mutual close plans, executive business reviews, and competitive displacement playbooks.
  • Develop an account-based strategy for the top 50 target accounts with dedicated pursuit plans, relationship maps, and executive engagement cadences.
• Customer Retention & Expansion
  • Drive gross revenue retention from current levels to 92%+ through proactive customer health monitoring, risk identification, and executive intervention processes.
  • Own the net revenue retention number, targeting 110%+ through systematic expansion and cross-sell into the installed base.
  • Establish executive-level relationships with top accounts, ensuring strategic alignment and long-term partnership positioning.
  • Implement a structured customer lifecycle management process from onboarding through renewal, with clear ownership, milestones, and escalation paths.
• Global Team Leadership
  • Lead and scale a global revenue organization encompassing Sales (Enterprise and Mid-Market), Marketing (Demand Gen, Product Marketing, Field Marketing), Business Development (SDR/BDR), Customer Success, and Revenue Operations.
  • Build a performance-driven culture with clear accountability, transparent metrics, and a low-tolerance approach to underperformance—while maintaining a supportive, coaching-oriented environment for top performers.
  • Recruit, develop, and retain A-level talent across all revenue functions, with a particular emphasis on hiring missionaries who demonstrate ownership mentality and independent judgment.
  • Manage distributed teams across time zones with disciplined operating rhythms, clear communication protocols, and consistent performance management.
• Unit Economics & Profitable Growth
  • Maintain and improve unit economics as the company scales: CAC payback under 18 months, LTV-to-CAC ratio above 3x, and gross margins consistent with best-in-class SaaS benchmarks.
  • Make resource allocation decisions based on data, not instinct—investing in segments, channels, and motions that demonstrate efficient returns and pulling back from those that do not.
  • Provide the CEO and board with clear, honest reporting on revenue performance, pipeline health, retention trends, and forward-looking indicators.

Qualifications

• Proven track record scaling a B2B SaaS company from $20–40M to $100M+ ARR as CRO, VP of Sales, or equivalent revenue leadership role.
• Direct, personal experience closing six- and seven-figure enterprise deals with Fortune 500 or equivalent large enterprise customers.
• Experience leading a global, multi-functional revenue organization including Sales, Marketing, and Business Development with 50+ total team members.
• Demonstrated ability to build and operate a demand generation engine that produces predictable, inspectable pipeline across multiple channels.
• Deep understanding of modern SaaS unit economics including CAC, LTV, payback period, gross margin, GRR, and NRR—with evidence of running a profitable or capital-efficient operation.
• Experience implementing or scaling a product-led growth motion alongside traditional enterprise sales.
• Track record of improving gross revenue retention to 90%+ and net revenue retention to 110%+ at scale.
• Experience selling into regulated industries (financial services, healthcare, government, life sciences) with complex compliance and security requirements.
• Minimum 15 years of progressive revenue leadership experience, with at least 5 years in a CRO or equivalent role.

Strongly Preferred

• Experience in the Salesforce ecosystem or adjacent enterprise platform ecosystems.
• Background in DevOps, DevSecOps, or developer tools with an understanding of how technical buyers evaluate and adopt platform solutions.
• Experience at a bootstrapped or capital-efficient company (not solely venture-backed hypergrowth environments where profitability was not a constraint).
• Familiarity with multi-product portfolio selling and the orchestration of cross-sell and land-and-expand motions.
• Experience building and leveraging executive communities or advisory boards as a strategic GTM channel.
• History of competitive displacement wins against well-funded or market-leading competitors.

Benefits

• Competitive compensation, incentive structure, and company equity.
• Daily coaching, mentorship, and growth opportunity.
• Remote-first team!
• Be part of a global, mission-driven team.
• Learn from top leaders in Salesforce DevOps and SaaS sales.
• Work on exciting challenges in a rapidly growing industry.
• Unlimited Flex Time Off Plan + All Major holidays.

Compensation & Structure

• Compensation will be commensurate with experience and structured to reward performance:
• Competitive base salary reflecting the CRO-level scope and enterprise SaaS benchmarks.
• Significant performance-based variable compensation tied to bookings, retention, and profitability targets—not vanity metrics.
• Equity participation with meaningful upside tied to the $30M-to-$100M growth trajectory.
• Clear quarterly milestone structure with transparent measurement and payout criteria.