Matt Crane

Sales Engineer

OnRamp

Sales EngineerOutbound HeavyEnterpriseOn-site📍 Boston, MA (Fort Point)
Deal Size: $100K-500K+ ACV
Sales Cycle: 3-6 months
Posted by Matt Crane

Overview

You're a Sales Engineer at OnRamp supporting AEs on mid-market and enterprise deals. You run technical demos, build custom POCs, and answer security/integration questions. You're proving OnRamp can handle complex onboarding at scale—Fortune 15 use cases like Cardinal Health onboarding thousands of pharmacy customers, or Bullhorn's self-serve SMB motion.


Role Snapshot

AspectDetails
Role TypePre-sales SE (some post-sales handoff)
Sales MotionOutbound-heavy (supporting AE pipeline)
Deal ComplexityEnterprise and Strategic
Sales Cycle3-6 months (enterprise deals you support)
Deal Size$100K-500K+ ACV (larger deals need SE support)
Quota (est.)Revenue influence, not direct quota

Company Context

Stage: Series A (raised Q4 2024, scaling fast)

Size: ~12-15 employees (just tripled GTM team)

Growth: From 1 sales rep to landing 3 Fortune 15 customers in 2 years. Adding multiple AEs, SDRs, SEs, Rev Ops.

Market Position: Proving enterprise buyers will pay for purpose-built customer onboarding platforms vs homegrown or CS platform add-ons.


GTM Reality

Pipeline Sources:

  • 75% Outbound - AEs are running deals from SDR-sourced pipeline
  • 25% Inbound - Demo requests, referrals, expansion within existing accounts

SDR/AE Structure: SDRs book, AEs run sales process. You support AEs on technical aspects.

SE Support: You're building the SE function. Might be the first or second SE hire.


Competitive Landscape

Main Competitors: Homegrown tools, Gainsight onboarding modules, Arrows, CS platform add-ons

How They Differentiate: Built for scale. Fortune 15 proof points. Handles both high-touch and self-serve use cases.

Common Objections: "We built something internally," "Our CS platform does this," "Security/compliance concerns," "Integration lift is too high"

Win Themes: Scalability, reduced CS team burden, faster time-to-value, proven at enterprise scale


What You'll Actually Do

Time Breakdown

Technical Demos (40%) | POCs/Pilots (30%) | Security/Integration Discovery (20%) | Internal (10%)

Key Activities

  • Technical Demos: Showing how OnRamp works under the hood. Walking through integrations (CRM, CS platform, product data). Demonstrating customization for their specific onboarding flow.
  • POCs and Pilots: Building custom configurations for 30-60 day trials. Setting up test environments. Working with their IT/Implementation teams to prove it works at their scale.
  • Security and Compliance: Answering security questionnaires. Walking IT through SOC 2, data handling, encryption, access controls. This is table stakes for enterprise.
  • Integration Discovery: Figuring out what systems OnRamp needs to connect to (Salesforce, HubSpot, Gainsight, Zendesk, their product APIs). Scoping technical lift for implementation.
  • Implementation Handoff: After deal closes, briefing CS/Implementation team on what was promised in the sale. Sometimes helping with initial setup.

The Honest Reality

What's Hard

  • Early-stage product means features are still being built. You'll hear "can it do X?" and sometimes the answer is "not yet, but it's on the roadmap."
  • Enterprise POCs are time-intensive. You're juggling multiple pilots at once, each with custom requirements.
  • Technical debt from fast growth. The product works at Fortune 15 scale, but documentation and internal knowledge sharing are catching up.
  • Balancing pre-sales and post-sales. AEs want you in every deal, but customers need help after they buy too.

What Success Looks Like

  • High POC-to-close conversion rate (your demos and pilots prove value)
  • Short time-to-POC (you can spin up trials quickly)
  • Few post-sale surprises (what you demo is what they get)
  • AEs trust you to handle technical conversations without them

Who You're Selling To

Primary Buyers:

  • VP/Chief Customer Officer (economic buyer, less technical)
  • VP Customer Success (champion, semi-technical)
  • Head of Implementation (end user, very technical)
  • IT/Security teams (gatekeepers, highly technical)

What They Care About:

  • Can it integrate with our stack? (CRM, CS platform, product, data warehouse)
  • How long does implementation take?
  • Security, compliance, data handling
  • Can it scale to our volume? (10 customers vs 10,000)

Requirements

  • 2-4 years as an SE or Solutions Consultant in B2B SaaS
  • Technical enough to understand APIs, integrations, data flows
  • Experience with CS/CX tech stack (Salesforce, Gainsight, Zendesk, etc.)
  • Comfortable building POCs and running pilots
  • In office every day in Fort Point, Boston (team is there daily)
  • Okay with early-stage chaos—you're building SE processes from scratch