Overview
You own the post-sale relationship for construction and infrastructure fleet companies using Gearflow's AI-powered procurement platform. These are fleet managers, equipment coordinators, and operations folks managing parts, service, and equipment for construction crews. Your job is retention first, expansion second - keep them using the platform, get more of their team on it, prevent churn.
Role Snapshot
| Aspect | Details |
|---|---|
| Role Type | Post-sale CSM (retention + expansion) |
| Sales Motion | Reactive support + proactive check-ins + upsell outreach |
| Deal Complexity | Consultative (adoption/change management focus) |
| Sales Cycle | N/A for retention, 4-8 weeks for expansions |
| Deal Size | Base contracts likely $10-50K/year, expansions $5-20K |
| Quota (est.) | Likely measured on retention rate (>90%) + expansion ARR ($150-300K/year) |
Company Context
Stage: Early-stage (20 employees suggests Seed or Series A)
Size: 20 employees
Growth: Hiring for CS suggests they're past initial PMF and scaling customer base
Market Position: Niche player - targeting a specific vertical (construction/fleet) that's traditionally underserved by modern procurement software. Not a crowded space, but also not a proven category.
GTM Reality
Your Customer Base: You're likely managing 20-40 accounts (at their size, probably on the higher end). These are construction companies, infrastructure contractors, equipment rental operations. Buyers are fleet managers, operations directors, project managers - practical operators, not tech-savvy SaaS buyers.
Support Model: At 20 people total, you're probably one of 1-2 CS people. You're doing everything - onboarding, training, support tickets, check-ins, renewals, upsells. No dedicated support team to offload tier-1 issues to.
Product Maturity: Early product means bugs, missing features, and customers asking for things that don't exist yet. You'll be the voice of the customer internally, which is good for impact but frustrating when things don't get built.
Competitive Landscape
Main Competitors: Likely competing against legacy systems (spreadsheets, email chains, phone calls to suppliers) more than other software. Some may use generic procurement tools or fleet management software that doesn't specialize in their workflow.
How They Differentiate: AI-powered procurement specifically built for heavy equipment fleets. The pitch is it's built for their specific use case vs generic tools.
Common Objections from Customers:
- "This is another system for my team to learn"
- "We've always done it this way"
- "My guys aren't tech people"
- "I need this feature you don't have yet"
Win Themes: Time savings, reduced errors, better visibility into spend/orders, empowering field teams.
What You'll Actually Do
Time Breakdown
Customer Support (35%) | Proactive Check-ins (30%) | Expansion/Upsell (15%) | Internal Meetings (20%)
Key Activities
- Reactive Support: Field questions via email, Slack, or calls. "How do I do X?" "This isn't working" "Can you add this user?" A lot of basic platform questions because your users are busy operators, not software power users.
- Onboarding New Users: When a customer adds team members or locations, you're training them. Usually screen-shares walking through the platform. Repetitive but necessary.
- Quarterly Business Reviews: Scheduled check-ins with key accounts (maybe 1-2/week). You pull usage data, show them their activity, talk about what's working and what's not. These often surface feature requests you can't fulfill yet.
- Expansion Conversations: Identifying accounts that could add more users, locations, or use cases. This is your "sales" motion - trying to expand contract value. Success rate depends heavily on how well the platform is working for them already.
- Internal Escalations: You're the customer advocate. When something breaks or a customer needs a feature, you're documenting it and pushing product/engineering. At a 20-person company, you probably have decent access, but resources are limited.
- Renewal Prep: For accounts coming up on renewal, you're assessing health, addressing concerns, negotiating terms. At this stage, probably working closely with founders/leadership on bigger renewals.
The Honest Reality
What's Hard
- Customer Sophistication: You're supporting fleet managers who manage bulldozers, not software. Many aren't comfortable with new platforms. Lots of hand-holding on basic tasks.
- Product Gaps: Early-stage product means customers will hit limitations. You'll hear "why can't it do this?" frequently. You can't magically build features, which strains relationships.
- Churn Risk: If the platform doesn't save them meaningful time or money, they'll churn. Construction is a tough, margin-sensitive business. They won't pay for tools that don't work.
- Wearing Multiple Hats: You're support, training, account management, and expansion sales. No specialization means you're constantly context-switching.
- Usage Enforcement: Getting customers actually to USE the platform is hard. Adoption drops off after initial enthusiasm. You'll spend time trying to re-engage inactive users.
What Success Looks Like
- Retention: Keeping >90% of ARR renewed. At this stage, every logo matters.
- Expansion: Adding $150-300K in expansion ARR annually (new seats, new locations, add-on modules).
- Product Champion: Customers actively using the platform, giving good feedback, willing to be references.
- Proactive Problem-Solving: Catching issues before customers churn. Usage drops? You're on it. Haven't logged in? You're calling.
Who You're Supporting
Primary Users:
- Fleet managers at construction/infrastructure companies
- Equipment coordinators
- Project managers who need to order parts/service
- Operations directors overseeing multiple sites
What They Care About:
- Not breaking their workflow: If your platform slows them down, they'll stop using it.
- Tangible ROI: Time saved, money saved, fewer errors. They need to justify the cost.
- Reliability: Construction doesn't stop. If they need a part urgently and your platform is down, that's a crisis.
- Ease of Use: Their teams are field workers, not office workers. Complex UIs don't fly.
Requirements
- 2-4 years in customer success, account management, or support (B2B SaaS preferred but not required)
- Comfortable with blue-collar customers - you need to relate to fleet managers and construction operators, not just talk SaaS jargon
- Self-sufficient problem solver - small team means you figure things out yourself
- Willing to do the grunt work - this isn't a strategic "executive sponsor" role, you're in the weeds daily
- Thick skin for customer frustration - when things break or don't work as expected, you're the one hearing about it
- Genuine interest in helping people (the "hungry and humble" line suggests they want someone who cares, not just someone checking boxes)