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.

Highlights

• Employees across Canada and the United States, with an office in Saskatoon

• 74 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 platform

• 98% customer retention rate — one of the strongest signals of product-market fit in enterprise SaaS

• Flagship 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 US

  • Best Workplaces, Canada (under 100) 

  • Best Workplaces in Technology, Canada  

• Named 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 Revenue

• Personally lead Andgo's largest enterprise opportunities, strategic accounts, partnerships, and commercial negotiations

• Build executive relationships and navigate complex, multi-stakeholder sales cycles — including security and compliance reviews, procurement negotiations, technical evaluations, and C-suite steering committees

• Develop quantified, compelling business cases covering labor efficiency, staffing outcomes, compliance, operational risk, retention, productivity, and ROI

• Secure customer design-partners for Andgo's emerging AI-enabled offerings and convert successful pilots into recurring, enterprise-wide contracts

• Represent Andgo in any growth-capital processes

Coach — Build an Elite GTM Team

• Evaluate and enhance the effectiveness of the existing commercial structure, territories, incentives, and team performance

• Recruit high performers into the commercial organization and develop enterprise sales, marketing, Customer Success, account management, value engineering, and RevOps talent

• Coach the team through regular deal reviews, customer meetings, business-case development, and negotiations

• Strengthen executive selling techniques, healthcare-domain knowledge, value-based selling, and land-and-expand capabilities across the team

• Establish clear expectations for pipeline development, funnel velocity, forecasting, quota attainment, retention, and expansion

Process Builder — Create a Predictable Revenue System

• Define ideal customer profiles, priority segments, target buyers, use cases, positioning, territories, and coverage models

• Establish consistent qualification, discovery, value-selling, deal-review, forecasting, and negotiation best practices across the commercial team

• Align Marketing, Sales, Implementation, Customer Success, and Account Management around clear ownership, accountability, and handoffs

• Modernize 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 margin

• Establish packaging and pricing for recurring software, AI usage, implementation, and tech-enabled services

• Develop consistent ROI models using customer data, relevant benchmarks, and defensible assumptions

Full Lifecycle Ownership

• Own the complete customer journey — from market positioning and demand generation through enterprise sales, implementation handoff, adoption, expansion, and renewal

• Win new enterprise customers in healthcare and emerging verticals (manufacturing and beyond) while protecting and growing the existing revenue base

• Build the bridge between Customer Success and sales — ensuring Andgo's proven ROI translates into referrals, referenceable case studies, and expansion revenue

• Ensure incentives reward profitable, sustainable revenue and avoid low-quality bookings, uneconomic pilots, or excessively customized services

Strategy & Board Partnership

• Serve as a strategic advisor to the CEO and Board on all matters of growth, pipeline, market strategy, pricing, unit economics, and organizational capability

• Present an executable 12–24-month revenue plan within the first 90 days

• Drive 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 stakeholders

• Full 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 transformation

• A track record of building scalable, repeatable GTM processes and bringing greater predictability to the full revenue cycle

• Commercially rigorous — distinguishes evidence-based pipeline from seller optimism; makes decisions from data

• Full-funnel oriented — treats acquisition, adoption, retention, and expansion as one integrated commercial system, not separate functions

• Executive presence and storytelling ability — communicates complex commercial dynamics clearly to customers, employees, the Board, and investors

• Low ego, high integrity — works effectively across functions, seeks feedback, and prioritizes long-term customer value

• Adaptable — comfortable commercializing offerings before every element is fully established

• Canada or US-based

Bonus:

• Experience commercializing AI, analytics, automation, or decision-support products

• Enterprise healthcare SaaS, workforce management, labor optimization, or clinical operations background

• Familiarity with outcome-based, usage-based, or hybrid pricing models

• Exposure to union-environment customers or complex compliance-driven enterprise sales cycles

The Extras that Matter

• Competitive base salary + performance-based variable tied directly to revenue outcomes

• Comprehensive health and dental benefits

• Fully distributed team - work from anywhere in Canada or the United States with genuine flexibility

• First CRO hire in company history — real authority, real ownership, real impact from day one

• A product with 100% customer retention and a 300%+ demonstrated ROI — the hardest part of the sales job is already done

• A new AI platform in market and new verticals opening — the timing is right and the commercial surface area is expanding

• Direct access to a founder-CEO who is invested in getting this hire right and treating this person as a long-term partner in the business

• Equity participation — this hire is being treated as a strategic partner, not just an executive

• A team and culture that's been recognized as one of Canada's Top Small and Medium Employers and a Saskatchewan Top Employer