Chief Revenue Officer

Andgo Systems is a rapidly growing SaaS company transforming how complex organizations manage workforce staffing. Its intelligent shift-fill automation platform helps healthcare and other complex, high-volume organizations automate absence reporting, shift matching, notifications, vacation mapping and workforce communication — enabling them to fill more shifts, faster, with the right people. Andgo has established a strong position in healthcare workforce automation across Canada and the United States. What began as a healthcare-focused scheduling tool has evolved into an intelligent automation suite that's now expanding beyond health systems into manufacturing and other complex scheduling environments. The platform covers shift filling, vacation mapping, absence management, broadcast communication, and shift prebooking — all configurable to fit the union rules, call list hierarchies, and compliance requirements that make these environments so difficult to manage. Andgo integrates seamlessly with major scheduling systems including UKG, and is trusted by large, complex organizations with thousands of employees across multiple locations. Now in an active AI platform transition, Andgo is launching its next-generation AI-enabled workforce management platform and entering a defining growth chapter. The product has proven enterprise ROI at scale. The customer base is loyal. The pipeline is real. What's needed now is the commercial architecture to match — and the leader to build it. HighlightsEmployees across Canada and the United States, with an office in Saskatoon74 employees, growing 24.6% YoY (+17 people in the last year)$6.2M raised across two funding rounds: Series A co-led by First Ascent Ventures and Waterline Ventures to accelerate its intelligent workflow automation platform98% customer retention rate — one of the strongest signals of product-market fit in enterprise SaaSFlagship clients: Works with the largest healthcare organizations throughout North America such New York Presbyterian, Vancouver Coastal Health, Advent Health to name a few.Active AI platform transition underway — new product in market, expanding into manufacturing and new verticals"Great Pleace to Work" certified in Canada and the USBest Workplaces, Canada (under 100)Best Workplaces in Technology, CanadaNamed the 2025 Deloitte Technology Fast 500 for the third consecutive year, recognizing its continued growth among North America's fastest-growing technology companies About the Role This is Andgo's first dedicated Chief Revenue Officer — a milestone hire that signals exactly where the company is headed. The commercial foundation exists: a loyal enterprise customer base, a product with proven ROI, and a GTM team in place. What hasn't existed until now is a unified commercial architecture, a scalable revenue operating system, and a senior leader who owns the full picture from market positioning through multiyear renewal. That changes with this hire. The CRO will report directly to CEO Tom Ross and will own all revenue-generating activity at Andgo — Sales, Marketing, Customer Success, Partnerships, and RevOps — unified around a single, coherent go-to-market strategy. The mandate is clear: commercialize Andgo's new AI-enabled platform, build a credible path to $50M ARR, win new enterprise customers, and protect and grow the existing revenue base. This is a player-coach-process builder role in equal measure. The CRO will personally lead Andgo's most strategically important deals while building the team, the systems, and the culture that sustains growth long after the first wins. Player — Develop Opportunities & Close RevenuePersonally lead Andgo's largest enterprise opportunities, strategic accounts, partnerships, and commercial negotiationsBuild executive relationships and navigate complex, multi-stakeholder sales cycles — including security and compliance reviews, procurement negotiations, technical evaluations, and C-suite steering committeesDevelop quantified, compelling business cases covering labor efficiency, staffing outcomes, compliance, operational risk, retention, productivity, and ROISecure customer design-partners for Andgo's emerging AI-enabled offerings and convert successful pilots into recurring, enterprise-wide contractsRepresent Andgo in any growth-capital processesCoach — Build an Elite GTM TeamEvaluate and enhance the effectiveness of the existing commercial structure, territories, incentives, and team performanceRecruit high performers into the commercial organization and develop enterprise sales, marketing, Customer Success, account management, value engineering, and RevOps talentCoach the team through regular deal reviews, customer meetings, business-case development, and negotiationsStrengthen executive selling techniques, healthcare-domain knowledge, value-based selling, and land-and-expand capabilities across the teamEstablish clear expectations for pipeline development, funnel velocity, forecasting, quota attainment, retention, and expansionProcess Builder — Create a Predictable Revenue SystemDefine ideal customer profiles, priority segments, target buyers, use cases, positioning, territories, and coverage modelsEstablish consistent qualification, discovery, value-selling, deal-review, forecasting, and negotiation best practices across the commercial teamAlign Marketing, Sales, Implementation, Customer Success, and Account Management around clear ownership, accountability, and handoffsModernize the RevOps technology stack, data infrastructure, and reporting — build dashboards covering pipeline coverage, conversion, sales velocity, win rate, ARR/MRR, NRR, forecast accuracy, LTV/CAC, payback period, and gross marginEstablish packaging and pricing for recurring software, AI usage, implementation, and tech-enabled servicesDevelop consistent ROI models using customer data, relevant benchmarks, and defensible assumptionsFull Lifecycle OwnershipOwn the complete customer journey — from market positioning and demand generation through enterprise sales, implementation handoff, adoption, expansion, and renewalWin new enterprise customers in healthcare and emerging verticals (manufacturing and beyond) while protecting and growing the existing revenue baseBuild the bridge between Customer Success and sales — ensuring Andgo's proven ROI translates into referrals, referenceable case studies, and expansion revenueEnsure incentives reward profitable, sustainable revenue and avoid low-quality bookings, uneconomic pilots, or excessively customized servicesStrategy & Board PartnershipServe as a strategic advisor to the CEO and Board on all matters of growth, pipeline, market strategy, pricing, unit economics, and organizational capabilityPresent an executable 12–24-month revenue plan within the first 90 daysDrive Andgo's commercial narrative with customers, investors, partners, and the Board About You This is a true builder role. The incoming CRO will own Andgo’s revenue engine across sales, marketing, expansion, upsell, and potentially customer experience. We’re looking for someone who has built and scaled before — not someone whose experience has primarily been operating within an established commercial machine.Proven track record in AI-enabled software or tech services, with experience scaling revenue from $15M to $50M+Hands-on enterprise seller — capable of opening strategic accounts and personally closing 7-figure, 6–12+ month complex deals across technical, compliance, financial, and clinical stakeholdersFull lifecycle fluency — mastery of the entire customer journey (acquisition through multiyear renewal) and the unit economics behind it (ARR, NRR, LTV/CAC, gross margin, pipeline health)Experience recruiting, coaching, and upskilling GTM teams through commercial transformationA track record of building scalable, repeatable GTM processes and bringing greater predictability to the full revenue cycleCommercially rigorous — distinguishes evidence-based pipeline from seller optimism; makes decisions from dataFull-funnel oriented — treats acquisition, adoption, retention, and expansion as one integrated commercial system, not separate functionsExecutive presence and storytelling ability — communicates complex commercial dynamics clearly to customers, employees, the Board, and investorsLow ego, high integrity — works effectively across functions, seeks feedback, and prioritizes long-term customer valueAdaptable — comfortable commercializing offerings before every element is fully establishedCanada or US-basedBonus:Experience commercializing AI, analytics, automation, or decision-support productsEnterprise healthcare SaaS, workforce management, labor optimization, or clinical operations backgroundFamiliarity with outcome-based, usage-based, or hybrid pricing modelsExposure to union-environment customers or complex compliance-driven enterprise sales cycles The Extras that MatterCompetitive base salary + performance-based variable tied directly to revenue outcomesComprehensive health and dental benefitsFully distributed team - work from anywhere in Canada or the United States with genuine flexibilityFirst CRO hire in company history — real authority, real ownership, real impact from day oneA product with 100% customer retention and a 300%+ demonstrated ROI — the hardest part of the sales job is already doneA new AI platform in market and new verticals opening — the timing is right and the commercial surface area is expandingDirect access to a founder-CEO who is invested in getting this hire right and treating this person as a long-term partner in the businessEquity participation — this hire is being treated as a strategic partner, not just an executiveA team and culture that's been recognized as one of Canada's Top Small and Medium Employers and a Saskatchewan Top Employer