David Freeman OLY, MBA

Senior Revenue Operations Analyst

TurboTenant

Revenue OperationsPLG AssistedConsultative📍 Denver, Colorado
Deal Size: $500-$5K ACV
Sales Cycle: 2-6 weeks
Posted by David Freeman OLY, MBA•

Overview

You're the first dedicated RevOps hire at a 101-person proptech company that sells rental property management software to independent landlords. You'll build the revenue operations function from scratch—owning HubSpot configuration, data architecture, process documentation, and reporting for the go-to-market teams.


Role Snapshot

AspectDetails
Role TypeRevenue Operations Analyst - foundational build
Sales MotionLikely PLG-assisted (they offer a free plan) with outbound
Deal ComplexityTransactional to consultative (SMB landlords)
Sales CycleProbably 2-6 weeks for paid conversions
Deal SizeLikely $500-$5K ACV (SMB SaaS pricing)
Quota (est.)N/A - enablement role

Company Context

Stage: Unknown funding stage, likely Series A/B based on size

Size: 101 employees

Growth: Actively hiring RevOps, signals investment in GTM infrastructure

Market Position: Competing in crowded landlord software space (Buildium, AppFolio, Rent Manager, Cozy, Avail)


GTM Reality

Pipeline Sources:

  • Likely heavy inbound from free plan users converting to paid
  • Content marketing to landlords (educational SEO)
  • Some outbound to property managers with small portfolios
  • Word of mouth in landlord communities

SDR/AE Structure: Unknown, but at 101 people likely has dedicated sales team

SE Support: Unlikely for this market—product demos are probably straightforward


Competitive Landscape

Main Competitors: Buildium, AppFolio, Rent Manager, Avail, Cozy (now owned by Apartments.com)

How They Differentiate: Free plan with robust features, focused on independent landlords vs. large property management companies

Common Objections: "I'm already using spreadsheets and it's free," "I only have 2-3 properties, do I really need this?", "How is this different from [competitor]?"

Win Themes: Ease of use, time savings on manual tasks, all-in-one platform vs. duct-taped solutions


What You'll Actually Do

Time Breakdown

HubSpot Admin (35%) | Data/Reporting (30%) | Process Design (20%) | Meetings (15%)

Key Activities

  • HubSpot Configuration: Building workflows, custom properties, pipeline stages, automation, and integrations. You're the system admin for the entire CRM. When something breaks or needs to be added, it's on you.
  • Data Architecture: Cleaning up messy data, standardizing field usage, building data hygiene processes. Right now data is probably inconsistent—different reps use fields differently, duplicate records exist, reporting is manual.
  • Reporting & Dashboards: Building and maintaining revenue dashboards, pipeline reports, conversion metrics, and forecasting models. Expect lots of "can you pull a report on X" requests.
  • Process Documentation: Writing down how things should work (lead routing, deal stages, handoff processes) because it's probably mostly tribal knowledge right now. You'll sit in sales meetings figuring out what actually happens vs. what should happen.
  • Stakeholder Management: Talking to sales, marketing, customer success, and finance to understand their needs and priorities. You're translating business needs into system requirements.
  • Tool Evaluation: Researching and potentially implementing new tools (enrichment, email automation, analytics) as the stack matures.

The Honest Reality

What's Hard

  • Building from scratch means no blueprint: There's no existing documentation or process to reference. You're figuring out what "right" looks like while also implementing it.
  • Everyone wants something different: Sales wants one thing, marketing wants another, finance wants clean data for board decks. You're constantly prioritizing competing requests with limited bandwidth.
  • Data is messy: Historical data is inconsistent. You'll spend significant time cleaning up before you can build anything reliable on top of it.
  • You're a cost center: RevOps doesn't directly generate revenue, so when growth slows, you might feel pressure or have to justify projects. Results are often invisible until something breaks.
  • Ambiguous scope: "RevOps" means different things to different people. You'll need to define your own role boundaries and fight scope creep.

What Success Looks Like

  • Sales reps spend less time on admin work and more time selling because processes are automated
  • Leadership has accurate, real-time pipeline visibility instead of relying on spreadsheet updates
  • Forecasting accuracy improves because data is clean and stages are standardized
  • New reps onboard faster because systems and processes are documented
  • You build a roadmap and execute on it independently without constant direction

Who You're Supporting

Primary Stakeholders:

  • Sales leadership (VP Sales or Head of Sales) - wants pipeline visibility and forecasting
  • AEs and SDRs - want efficient workflows and less manual data entry
  • Marketing - wants lead routing, attribution, and campaign reporting
  • Finance - wants revenue reporting and commission data

What They Care About:

  • Sales: "Make my CRM easier to use and stop asking me to update fields manually"
  • Marketing: "Tell me which campaigns are actually generating pipeline"
  • Leadership: "Give me accurate forecasts and help us scale without adding more headcount"

Requirements

  • 3-5+ years in revenue operations, sales operations, or marketing operations
  • Expert-level HubSpot experience (you should know the platform inside and out, not just basic admin)
  • Strong data analysis skills - comfortable with SQL or advanced Excel/Google Sheets
  • Experience building processes and workflows from scratch (not just maintaining existing systems)
  • Ability to work independently with ambiguous problems
  • Bonus: Experience in B2B SaaS, especially PLG or SMB motions
  • Bonus: Salesforce to HubSpot migration experience (they might be considering it)