Overview
You're building outbound pipeline for PassBy, a retail intelligence platform that uses AI to analyze customer foot traffic and behavior. You'll be prospecting into multi-location retailersârestaurant groups, coffee chains, apparel brandsâtrying to book demos for whoever's closing deals (likely the CRO at this stage). At 23 people total, this is early-stage GTM where you're figuring out messaging and ICP as you go.
Role Snapshot
| Aspect | Details |
|---|---|
| Role Type | Outbound SDR |
| Sales Motion | Outbound-heavy (90%+) |
| Deal Complexity | Consultative |
| Sales Cycle | 2-4 months (estimate for data/analytics tools to retailers) |
| Deal Size | $25-75K ACV (estimate based on multi-location retail market) |
| Quota (est.) | 15-20 qualified meetings/month |
Company Context
Stage: Early (23 employees, stage unknown but likely Seed/Series A)
Size: 23 employees
Growth: Hiring SDR + CSM suggests active customer base and expansion mode
Market Position: Niche player in retail analyticsâcompeting against foot traffic data providers, location intelligence platforms, and traditional retail analytics vendors
GTM Reality
Pipeline Sources:
- 90% Outbound - You're building lists and making cold calls/emails
- 10% Inbound - Minimal inbound at this stage; maybe some content/LinkedIn interest
- Partners/Referrals - Not a structured channel yet
SDR/AE Structure: You're likely the only SDR or one of two. You'll hand meetings to the CRO or a closing rep.
SE Support: Probably noneâdemos will be product-focused walkthroughs, not deep technical implementations.
Competitive Landscape
Main Competitors: Placer.ai (foot traffic analytics), Foursquare/FSQ (location data), traditional retail analytics consultancies, plus retailers' internal BI teams who think they can build this themselves.
How They Differentiate: AI-powered insights, real-world customer behavior data (not just transaction data), actionable intelligence for expansion/marketing decisions.
Common Objections: "We already track this internally," "How accurate is your data?", "This seems expensive for what we get," "We're not ready to buy another analytics tool."
Win Themes: Data they can't get elsewhere, faster insights than building in-house, specific use cases around site selection and marketing ROI.
What You'll Actually Do
Time Breakdown
Prospecting (60%) | Meeting Prep/Follow-up (25%) | Internal Sync (15%)
Key Activities
- List Building: You'll spend hours in LinkedIn Sales Nav and online directories identifying regional/national retail brands with 10+ locations. You need to find VP Ops, Directors of Real Estate, CMOs, or CFOs who care about expansion and store performance.
- Cold Calling: 50-70 dials per day to retail operators. Most won't pick up. When they do, you're pitching "data on where your customers are actually coming from" in 30 seconds before they hang up or say "send me something."
- Email Sequences: Multi-touch campaigns with subject lines about foot traffic trends or competitor location analysis. Low response rates (2-5%) are normal in B2B retail.
- Qualifying Conversations: When someone bites, you're asking how many locations they have, how they currently make expansion decisions, who owns site selection, and whether they have budget for analytics tools.
The Honest Reality
What's Hard
- Grinding Through No's: Retail operators get pitched constantly. Your connect rate will be low (5-10%), and most people don't think they need another data tool.
- Long, Unclear Sales Cycles: Even interested prospects take months to buy. They want to see ROI proof, run pilots, get budget approval. Deals slip all the time.
- Category Education: You're not selling a known category. Prospects often don't understand what you do until the third conversation, which means lots of dead-end meetings.
- Early-Stage Chaos: At 23 people, GTM is still being figured out. Your messaging will change, your ICP will shift, and you'll waste time chasing the wrong prospects.
What Success Looks Like
- Booking 15-20 qualified meetings per month (prospects with 10+ locations, budget authority, and active expansion/optimization plans)
- 30-40% of your meetings converting to next-stage opportunities
- Building a repeatable playbook for which retail segments respond and which don't
Who You're Selling To
Primary Buyers:
- VP/Director of Operations at multi-location retail brands
- Director of Real Estate/Site Selection at expanding chains
- CMOs or Marketing VPs looking for customer insights
What They Care About:
- "Will this help us pick better locations and avoid expensive mistakes?"
- "Can I prove ROI to justify the cost?"
- "How much work is it to implement and get value from this?"
- "Is the data actually accurate or is this directional guesswork?"
Requirements
- Comfortable making 50+ cold calls per day to senior retail execs who mostly won't pick up
- Ability to learn and explain a technical product (AI, data analytics) in simple terms to non-technical buyers
- Resilience through rejectionâmost prospects won't engage, and that's normal
- Self-starter mentalityâat 23 people, there's no big SDR team or structured onboarding; you'll figure a lot out yourself
- London-based (role is in-office)
- Previous SDR experience helpful but not required if you're scrappy and coachable