Chief Revenue Officer chez Flosum

Description

The Opportunity

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. Our customer base includes household-name brands, and our five-product portfolio creates significant expansion and cross-sell opportunity.

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. This is a company built by missionaries, not mercenaries—and we expect the same from our CRO.

The Product Portfolio

Our platform consists of five integrated product lines, all built 100% natively within the Salesforce ecosystem. This native architecture is a core competitive differentiator—no external servers, no third-party middleware, no security exposure points:

• DevOps — End-to-end release management, version control, CI/CD, and automated deployments for Salesforce environments. Designed for enterprise-scale complexity with full audit trails and compliance controls.
• Backup & Archive — Complete data protection with automated backup scheduling, granular recovery, and intelligent archival capabilities that help enterprises manage data lifecycle and reduce storage costs.
• Trust Center (Security & Compliance) — Proactive security scanning, vulnerability detection, and compliance monitoring that gives regulated enterprises real-time visibility into the health and security posture of their Salesforce environments.
• Data Seeding — Intelligent test data management that enables enterprises to create realistic, anonymized datasets for sandbox and development environments without exposing production data.
• DevOps for Veeva — Purpose-built release management for life sciences organizations running Veeva CRM on the Salesforce platform, addressing the unique regulatory and validation requirements of pharmaceutical and biotech companies.

The company has also integrated AI-powered capabilities into the platform, enabling intelligent automation across the DevOps lifecycle. The multi-product portfolio creates a powerful land-and-expand motion: the average deal size is increasing, and the cross-sell opportunity across the five product lines is substantial and largely untapped.

Requirements

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.

Required 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.

This role is not for everyone. It is for someone who has done this before—not someone who believes they can figure it out. It is for someone who runs toward problems, not away from them. Someone who holds themselves to a higher standard than anyone else could impose. Someone who understands that in a bootstrapped, profitable company, every decision carries real weight and every dollar matters.

If you are that person, we want to hear from you.

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.