Michael Hanna

Senior Manager, Revenue Operations

Undisclosed AI Enterprise Solution Company

Revenue OperationsBalancedEnterpriseHybrid📍 Toronto, ON
Deal Size: $100K-500K+ ACV
Sales Cycle: 3-9 months
Posted by Michael Hanna•

Overview

You're the founding RevOps manager at a fast-growing AI enterprise software company based in Toronto. Right now, you're a team of one—building the revenue operations function from the ground up. You'll spend your days in HubSpot configuring workflows, pulling pipeline reports for the CRO, troubleshooting data quality issues, and sitting in meetings with Sales, Marketing, and CS leaders trying to align on definitions and processes.


Role Snapshot

AspectDetails
Role TypePlayer-coach RevOps leader (IC work now, team building later)
Sales MotionSupporting enterprise AI sales (likely 3-9 month cycles)
Deal ComplexityEnterprise/Strategic (AI solutions require education + POCs)
Sales Cycle3-9 months (typical for enterprise AI)
Deal SizeLikely $100K-500K+ ACV (enterprise AI pricing)
Quota (est.)N/A (RevOps role)

Company Context

Stage: Early growth (likely Series A/B based on "fast-growing" + hiring senior RevOps)

Size: Unknown, but small enough that you're the first RevOps hire

Growth: Actively scaling sales team, adding enterprise customers

Market Position: Challenger in crowded AI space—need strong ops to compete efficiently


GTM Reality

Pipeline Sources:

  • Unknown split, but enterprise AI typically means:
    • 30-40% Outbound (SDR/BDR prospecting to specific enterprise accounts)
    • 30-40% Inbound (demo requests from website, marketing campaigns)
    • 20-30% Referrals/Partners (common in enterprise AI)

SDR/AE Structure: Likely have SDRs, but you'll need to figure out lead routing, SLAs, and handoff processes

SE Support: Probably have SEs or solution architects for technical demos and POCs


Competitive Landscape

Main Competitors: Unknown specifics, but competing in crowded enterprise AI space

How They Differentiate: Unknown—you'll need to learn this to build effective sales enablement

Common Objections: AI skepticism, integration complexity, data security concerns, ROI justification

Win Themes: You'll help Sales figure this out by analyzing closed-won deals in HubSpot


What You'll Actually Do

Time Breakdown

HubSpot Admin (30%) | Reporting/Analytics (25%) | Cross-functional Meetings (25%) | Process Design (20%)

Key Activities

  • HubSpot Configuration: Building and maintaining pipelines, deal stages, custom properties, workflows, and integrations. Fixing data quality issues when Sales enters garbage data. Training reps on how to actually use the CRM.
  • Reporting & Dashboards: Pulling weekly pipeline reviews for leadership. Building dashboards that answer "why are we missing quota?" Creating forecast models. Digging into conversion rates between stages to find bottlenecks.
  • Sales Process Design: Mapping out the ideal sales process, getting buy-in from AEs and managers, then realizing it doesn't work in practice and iterating. Documenting everything in Notion or Confluence that nobody reads.
  • Cross-Functional Alignment: Meetings with Marketing about lead quality and MQL definitions. Meetings with CS about expansion tracking. Meetings with Finance about commission calculations. A lot of meetings trying to get everyone to agree on basic definitions.
  • Tech Stack Evaluation: Researching and implementing AI-forward tools (conversation intelligence, sales engagement platforms, data enrichment). Managing vendor relationships. Fighting for budget.
  • Enablement Support: Creating territory plans, building compensation models, producing sales reports that actually get used.

The Honest Reality

What's Hard

  • You're building in a moving car: Sales process is changing as the company scales. What works at 5 AEs doesn't work at 15. You'll rebuild things multiple times.
  • Data is a mess: Reps don't follow processes. Duplicate records everywhere. Integration issues between tools. You'll spend hours cleaning data that gets dirty again next week.
  • Everyone wants different things: Sales wants fewer required fields. Marketing wants more attribution data. Finance wants airtight commission tracking. You're the referee.
  • Ambiguity: There's no playbook. You're figuring out what "AI-forward tech stack" even means for this company. Leadership expects you to know, but you're learning as you go.
  • Limited resources: You'll want to hire analysts and ops specialists, but you need to prove ROI first. Expect 6-12 months of solo IC work before you get budget for a team.

What Success Looks Like

  • Clean, trusted data: Leadership can look at the HubSpot dashboard and believe the numbers
  • Improved conversion rates: You identify that deals stall at the security review stage and implement a process that cuts that time in half
  • Forecast accuracy: Your pipeline analysis helps the CRO predict quarterly revenue within 10%
  • Team hire approved: You build such a solid foundation that you get budget to hire an analyst or ops coordinator

Who You're Working With

Key Stakeholders:

  • CRO or VP Sales (your direct boss, wants pipeline visibility)
  • VP Marketing (needs lead attribution and MQL definitions)
  • VP Customer Success (wants expansion tracking and churn analysis)
  • AEs and Sales Managers (your end users who complain about CRM changes)
  • Finance (needs accurate commission and revenue data)

What They Care About:

  • CRO: Can I trust the forecast? Where are deals getting stuck? How do I deploy reps efficiently?
  • Marketing: Are my campaigns generating revenue? What's the ROI on this event spend?
  • CS: Which accounts are at risk? What's our net retention rate?
  • AEs: Don't make me click more buttons. Just tell me what to do to hit quota.

Requirements

  • Deep HubSpot Sales Hub expertise (not just admin—you need to know advanced workflows, custom objects, reporting)
  • Experience at a scaling company (Series A/B stage) where you built ops processes from scratch
  • Comfort with AI tools and willingness to experiment with new tech (conversation intelligence, AI SDRs, predictive analytics)
  • Strong analytical skills—you can write SQL or at least manipulate data in Excel/Google Sheets to answer complex questions
  • Ability to influence without authority—you're not managing Sales/Marketing/CS, but need to change how they work
  • Hybrid work in Toronto area (likely 2-3 days/week in office for cross-functional collaboration)
  • Tolerance for ambiguity and changing priorities—this isn't a well-oiled machine yet