Michael Miele

Revenue Operations Manager

Vend Park

Revenue OperationsOutbound HeavyConsultative
Sales Cycle: 2-6 months
Posted by Michael Miele

Overview

You'll be the first dedicated Rev Ops hire building the revenue infrastructure at Vend Park, a 34-person company selling AI-powered parking management software to commercial real estate owners and property management teams. You work directly with the founder, COO, and revenue leadership to design and implement the systems, automation, and workflows that turn their scrappy two-year sales motion into something that scales to thousands of customers.


Role Snapshot

AspectDetails
Role TypeRevenue Operations Manager (first dedicated Rev Ops hire)
Sales MotionSupporting likely outbound-heavy commercial real estate sales
Deal ComplexityConsultative to enterprise (selling to property management companies)
Sales CycleLikely 2-6 months (real estate moves slowly)
Deal SizeUnknown - depends on property portfolio size
Quota (est.)N/A - measured on system efficiency, adoption, pipeline accuracy

Company Context

Stage: Early-stage (34 employees, founder posting directly suggests pre-Series A or early Series A)

Size: 34 employees

Growth: They explicitly say they've "figured out how to win customers" and are now focused on building systems to scale - classic inflection point between scrappy startup and growth stage

Market Position: Category player in parking tech (combining tech + operations), competing in a traditionally low-tech industry being digitized


GTM Reality

Pipeline Sources:

  • Likely 70-80% Outbound - selling into commercial real estate is relationship-heavy and requires targeted prospecting using tools like CoStar (CRE database)
  • 20-30% Referrals/Network - once you manage parking at one property, owners with multiple properties become natural expansion opportunities
  • Minimal Inbound - parking management software isn't something people Google; it's sold not bought

Current State: They've been selling for two years without formal Rev Ops, which means you're inheriting:

  • Inconsistent data in HubSpot
  • Manual processes that worked at 20 deals but break at 200
  • Tribal knowledge about what works
  • Tools that aren't talking to each other

Competitive Landscape

Main Competitors: Traditional parking management companies, legacy parking software, property management teams doing it manually

How They Differentiate: "Only AI-powered" solution that combines technology AND operations (they don't just sell software, they help run parking operations)

Common Objections: "Our current system works fine," switching costs, skepticism about AI actually working for parking

Win Themes: ROI through reduced labor costs, improved revenue capture, better driver experience


What You'll Actually Do

Time Breakdown

System Design/Implementation (40%) | Data/Process Cleanup (30%) | Reporting/Analysis (20%) | Training/Enablement (10%)

Key Activities

  • Build workflow automation: You're connecting HubSpot to Fireflies (call recording), ZoomInfo (prospecting data), and CoStar (CRE database). This means building Zapier/native integrations, designing data flows, and creating automated sequences that currently happen manually.
  • Clean up and structure CRM data: Two years of scrappy selling means messy data. You'll design field structures, implement data hygiene rules, dedupe records, and build dashboards that actually reflect reality.
  • Design territory and account assignment logic: Figure out how to segment their market (by property type? geography? portfolio size?), assign accounts to reps systematically, and create rules for when accounts get reassigned.
  • Build reporting infrastructure: Create pipeline dashboards, forecast models, activity tracking, and conversion metrics. You need to know: What activities lead to wins? Where do deals stall? What's a realistic close rate?
  • Implement AI/automation tools: They mention building infrastructure that makes small teams operate like large ones - this likely means evaluating and implementing AI SDR tools, automated email sequences, conversation intelligence from call recordings.
  • Document and train: Whatever you build only works if people use it. You'll create playbooks, run training sessions, and enforce adoption of new processes.

The Honest Reality

What's Hard

  • You're building from scratch with limited resources: No existing Rev Ops team, no documented processes, no clean historical data to analyze. Everything you need, you have to create.
  • You'll spend a lot of time on unglamorous data cleanup: Before you can build cool automation, you need to fix two years of inconsistent data entry, duplicate records, and missing fields.
  • Getting buy-in is constant work: Sales reps resist new processes. You'll have to convince people to log activities, follow new workflows, and adopt tools - while they're trying to hit quota.
  • You're the first hire, so expectations are vague: The founder knows they need "revenue systems" but may not know exactly what that means day-to-day. You'll need to set your own priorities and manage ambiguity.
  • Tools don't integrate as smoothly as promised: Connecting CoStar to HubSpot to Fireflies sounds clean but usually involves API limitations, workarounds, and manual CSV uploads.

What Success Looks Like

  • Pipeline forecast accuracy within 10-15% (currently probably way off)
  • Sales reps spending 20%+ more time on revenue-generating activities because admin is automated
  • Leadership can see real-time metrics on deal velocity, win rates, and rep performance without asking you to pull reports
  • New reps ramp 30-40% faster because there's actual documentation and structured onboarding
  • You've identified and plugged the biggest leaks in their funnel (where deals die, where reps waste time)

Who You're Supporting

You Work With:

  • Founder/CEO: You report to him directly - he cares about growth metrics, forecast accuracy, and whether the revenue engine is efficient
  • COO: Probably owns customer success/operations side - you'll align on data flows between sales and CS
  • Revenue Leadership: Likely a VP Sales or Head of Sales who needs pipeline visibility, territory planning, comp plan management
  • Sales Reps: Your actual end users who will complain when you change their workflows

What They Need From You:

  • Leadership wants: Accurate forecasts, clear metrics on what's working, confidence they can scale hiring
  • Reps want: Less admin work, easier prospecting, automation that helps them hit quota
  • You're constantly balancing: What leadership wants to measure vs. what's realistic to track vs. what reps will actually do

Requirements

  • 2-4 years in Rev Ops, sales ops, or related role (ideally at a B2B company that went through rapid scaling)
  • Strong HubSpot experience - you need to know it well enough to build complex workflows, custom objects, and reporting
  • Comfortable with data - SQL is a plus, but at minimum you can work with CSV exports, pivot tables, and build useful dashboards
  • Experience with sales tools (ZoomInfo, Outreach/Salesloft, call recording tools, enrichment platforms)
  • System design thinking - you see processes as systems, not one-off fixes
  • Comfortable with ambiguity and self-direction - there's no playbook for this role at Vend yet
  • Bonus: Experience in real estate tech, proptech, or selling to commercial real estate (you'll understand the buyer faster)
  • Bonus: Familiarity with AI tools and automation platforms (they're clearly betting on AI to scale efficiency)