Head of Sales Development

Overview

You run the SDR organization at AirGarage (managing managers who manage SDRs), but the real job is building the top-of-funnel machinery that generates pipeline for the entire sales team. You're architecting the AI tech stack, partnering with internal research teams to identify targets, and creating the systems that prioritize which parking lots to go after and how to convert them. You work directly with the VP Sales and future Head of Marketing to shape pipeline generation strategy for a 111-person company selling parking management software to lot owners.

Role Snapshot

Company Context

Stage: Growth stage (111 employees, funded but stage unknown)

Size: 111 employees

Growth: Actively hiring across GTM (VP Sales posting leadership roles)

Market Position: Modernizing a traditionally offline, fragmented industry (parking management)

GTM Reality

Pipeline Sources:

• 80%+ Outbound - parking lot owners don't search for software, you find them via research and outreach
• 10-15% Referrals - existing customers and property management networks
• 5-10% Inbound - some website traffic from lot owners googling "parking management software"

SDR/AE Structure: You manage the SDR managers who manage the SDRs. SDRs book meetings, AEs close.

SE Support: Unknown, likely light or none given parking management isn't deeply technical

Competitive Landscape

Main Competitors: Traditional parking operators (people with clipboards), legacy parking software, ParkMobile/SpotHero (consumer apps that also serve operators)

How They Differentiate: Full-service approach - enforcement, payment collection, visitor registration, support (vs point solutions)

Common Objections: "We already have a system" (person with a clipboard), "How do you handle enforcement?", "What if our tenants complain?", pricing vs doing it themselves

Win Themes: Hands-off management, better revenue capture, data/reporting they don't have today, enforcement without hiring staff

What You'll Actually Do

Time Breakdown

Pipeline Strategy (40%) | Team Leadership (30%) | Cross-functional (30%)

Key Activities

• Build the AI/Tech Stack: You're responsible for implementing and optimizing the tools that help identify which parking lots to target, score leads, automate outreach sequences, and route prospects. This is tech stack architecture and data work, not just buying software.
• Partner with Research Team: You work with AirGarage's internal research function to identify parking lot owners (public records, property data, commercial real estate databases). You turn raw data into targetable lists and prioritization frameworks.
• Manage SDR Managers: You have 1-2 SDR managers reporting to you. You coach them on team performance, help with hiring, set meeting quotas, review conversion metrics, and handle escalations. You're not in the day-to-day SDR coaching - that's their job.
• Shape Pipeline Strategy: You sit in planning meetings with VP Sales, Marketing leadership, and GTM leaders. You propose changes to ICP, territory splits, messaging, and lead routing. You own the "who we target and how" question.
• Report on Funnel Metrics: You build dashboards and report on leading indicators - meeting set rates, show rates, SQL conversion, pipeline coverage by segment. You spot problems early (a territory going cold, messaging not working, list quality dropping).
• Experiment and Iterate: You run tests - new messaging angles, different outreach sequences, alternative data sources. You measure what works and scale it, kill what doesn't.

The Honest Reality

What's Hard

• You're building systems from scratch - there's no playbook for "AI-powered parking lot prospecting." You need to figure out what works through trial and error.
• Parking lot owners are hard to reach - they're not on LinkedIn all day, they don't respond to cold emails well, and finding accurate contact info is a grind.
• You're managing managers, not reps - if your SDR managers aren't strong, you inherit their team's problems but can't fix them directly. You need to coach through them.
• The role is split between strategic work (building systems) and operational work (hitting pipeline targets). Some weeks you're in spreadsheets and data, other weeks you're in manager 1-on-1s and firefighting.
• Cross-functional dependency - you need Marketing to eventually own inbound, Research to deliver good data, Sales to close what you generate. If they underperform, your pipeline looks bad.

What Success Looks Like

• Your team consistently delivers the pipeline coverage ratio GTM needs (typically 3-4x quota coverage)
• Meeting set rates improve quarter over quarter because your targeting and messaging get smarter
• AEs tell you lead quality is going up - more qualified prospects, better fit, clearer pain
• You build automation that lets SDRs spend less time on admin and more time on conversations
• You hire and develop strong SDR managers who can run their teams without constant oversight

Who You're Selling To

Primary Buyers:

• Parking lot owners (individuals, small property groups)
• Commercial property managers (shopping centers, office buildings)
• Institutional real estate firms (larger portfolios)
• Municipalities (city-owned lots, some public parking)

What They Care About:

• Revenue maximization (are they leaving money on the table with current approach?)
• Operational headache reduction (don't want to hire/manage enforcement staff)
• Tenant/visitor satisfaction (complaints about parking hurt their core business)
• Compliance and liability (proper signage, ADA compliance, avoiding lawsuits)
• Data and reporting (most have zero visibility into utilization, revenue trends)

Requirements

• 5+ years in sales development or pipeline generation roles, with at least 2 years managing SDR managers (second-line leadership experience required)
• Track record of building or scaling SDR orgs - you've hired managers, designed comp plans, set quotas, and owned meeting/pipeline targets
• Experience with sales tech stack and automation - you've implemented tools (Outreach, Salesloft, Apollo, Clay, etc.) and know how to use data to improve conversion
• Comfort with ambiguity and building systems - this isn't a "run the playbook" role, it's a "create the playbook" role
• Cross-functional collaboration - you need to work well with Marketing, Research, Sales, and Ops without formal authority
• Analytical mindset - you look at funnel metrics, identify drop-off points, hypothesize fixes, and measure results
• Hands-on attitude - you'll jump into the details (reviewing call recordings, testing outreach copy, digging into data quality issues) when needed