Overview
You're closing deals with mid-market and enterprise companies that need to onboard external customers at scale. OnRamp helps B2B companies reduce churn, increase team capacity, and accelerate time-to-revenue. You're taking SDR-qualified meetings and running the full sales cycle - discovery, demo, multi-stakeholder meetings, proof of concept, negotiation, close. Your buyers are customer success VPs, onboarding directors, and operations leaders. You're in the office every day with the team in Fort Point.
Role Snapshot
| Aspect | Details |
|---|---|
| Role Type | Full-cycle AE (from SDR meeting to close) |
| Sales Motion | Outbound-heavy (75% of pipeline) |
| Deal Complexity | Consultative to Enterprise |
| Sales Cycle | 2-6 months (depending on company size) |
| Deal Size | $50K-$300K+ ACV |
| Quota (est.) | $600K-$1M+ annually |
Company Context
Stage: Series A (raised early Q4 2024)
Size: ~15-20 employees (tripled GTM in 3 months)
Growth: Fast scaling - went from 1 AE 2 years ago to multiple AEs now. Landed 3 Fortune 15 customers. High-velocity hiring across SDR, AE, SE, Rev Ops.
Market Position: Winning deals in a specific niche (external customer onboarding for B2B companies at scale). Competing against homegrown solutions and proving ROI vs. "just hire more people."
GTM Reality
Pipeline Sources:
- 75% Outbound - SDR team cold calling and emailing target accounts
- 25% Inbound - Some warm leads from website, referrals, and early brand awareness
SDR/AE Structure: Dedicated SDR team booking qualified meetings for you
SE Support: Yes - Sales Engineers help with technical demos and POCs for larger deals
Competitive Landscape
Main Competitors: Homegrown solutions (Notion, Airtable, Google Docs), customer success platforms adding onboarding features, generic workflow automation tools
How They Differentiate: Purpose-built for external customer onboarding (not internal employee onboarding). Proven at Fortune 15 scale. Measurable impact on churn and time-to-revenue.
Common Objections: "We've already built something internally", "Can we just add headcount instead?", "Our CS platform should handle this", "What if our onboarding process is too unique?"
Win Themes: Scalability (works for Fortune 15), reduces CS team manual work, quantifiable ROI on churn reduction and faster time-to-revenue, purpose-built vs. cobbled-together tools
What You'll Actually Do
Time Breakdown
Active Deals (50%) | Prospecting/Self-source (20%) | Internal/Forecast (20%) | Demo Prep (10%)
Key Activities
- Discovery calls: Understanding their current onboarding process (often manual, spreadsheet-based, or homegrown). Quantifying the pain - how much churn happens in first 90 days, how many hours CS reps spend on onboarding, how long until customers see value.
- Multi-stakeholder demos: Showing OnRamp to CS leaders, onboarding managers, ops teams, and sometimes IT/security. Tailoring the demo to their specific use case (SaaS onboarding, healthcare provider credentialing, staffing platform client setup, etc.).
- Building business cases: Working with champions to quantify ROI. You're projecting churn reduction, CS capacity gains, and time-to-revenue improvements. These deals need executive buy-in, so you're building slides and models.
- Managing technical evaluations: Coordinating POCs with the SE team. Larger deals (especially enterprise) want to test OnRamp with real customer data. You're project managing timelines, getting feedback, and troubleshooting issues.
- Navigating procurement: Enterprise deals involve legal, security reviews, vendor forms, and budget approvals. You're chasing signatures and keeping deals moving when they stall in procurement.
The Honest Reality
What's Hard
- You're competing against "do nothing" as much as competitors. Many companies have built homegrown onboarding processes and need convincing that OnRamp is worth ripping out and replacing.
- Deals involve multiple stakeholders - CS, ops, IT, security, legal, procurement. Getting everyone aligned takes time. Deals slip quarters.
- It's early stage. The sales process is still being refined. You're helping figure out what works - which means more ambiguity and iteration than at a mature company.
- You're in the office every day. This is not a remote role.
- Some deals are complex (Fortune 15 enterprises) and some are simpler (mid-market). You're learning to navigate both.
What Success Looks Like
- Closing $150K-$250K+ per quarter in new business
- Building a pipeline that's 3-4x your quarterly quota
- Winning competitive deals against homegrown solutions by demonstrating clear ROI
- Helping define the sales playbook that the next wave of AEs will use
Who You're Selling To
Primary Buyers:
- VP/Director of Customer Success (owns churn and NRR metrics)
- Head of Customer Onboarding/Implementation (feels the manual work pain daily)
- VP of Operations (cares about efficiency, scalability, cost per onboarded customer)
- CRO/COO (approves budget for larger deals)
What They Care About:
- Reducing early customer churn (onboarding is often where customers drop off or delay go-live)
- Scaling onboarding without proportionally scaling headcount
- Shortening time-to-revenue (customers signed but not using the product yet)
- Improving customer experience (less friction, fewer dropped balls, clearer progress)
- Measurable ROI (they need to justify the cost vs. hiring more onboarding specialists)
Requirements
- 2-4+ years in B2B SaaS sales, ideally selling to customer success or operations teams
- Comfortable running full-cycle deals from discovery to close with deal cycles of 2-6 months
- Can build business cases and ROI models - these deals need executive buy-in and quantifiable value
- Good at multi-threading - you're navigating CS, ops, IT, security, legal, and procurement
- Want to be in an office environment (Fort Point, every day) on an early-stage team where the playbook is still being written
- Okay with ambiguity and iteration - this isn't a mature sales org with defined processes