Derek Roberts

Customer Success Manager

OnRamp

Customer SuccessBalancedConsultative
Deal Size: $15-50K ACV base accounts, $5-25K expansions
Sales Cycle: 1-3 months for expansions
Posted by Derek Roberts

Overview

You manage ongoing relationships with B2B SaaS companies who use OnRamp's customer onboarding platform. You're responsible for adoption, retention, and finding expansion opportunities. You spend your time troubleshooting implementation issues, running QBRs, tracking product usage, and trying to grow accounts.


Role Snapshot

AspectDetails
Role TypeCSM - retention and expansion focused
Sales MotionExisting customer expansion, some renewal negotiations
Deal ComplexityConsultative - need to understand customer workflows
Sales CycleN/A for renewals (annual), 1-3 months for expansions
Deal SizeLikely $15-50K ACV base, expansions $5-25K
Quota (est.)Likely 95%+ net retention, $200-400K expansion annually

Company Context

Stage: Early-stage (59 employees, no public funding data available)

Size: 59 employees - small team, everyone wears multiple hats

Growth: Actively hiring, poster is a Post Sales Leader which suggests they're building out the CS function

Market Position: Customer onboarding/engagement space is crowded. Competing against point solutions and horizontal workflow tools that customers try to adapt.


GTM Reality

Your Book:

  • You likely own 20-40 accounts depending on ACV and complexity
  • Mix of implementation phase customers (high touch) and stable accounts (periodic check-ins)
  • You're probably the main point of contact - at this size there's no segmentation between onboarding specialists and CSMs

Support Structure:

  • At 59 people, there's probably minimal dedicated support - you handle most customer questions
  • Implementation likely falls on you unless they have a separate onboarding team
  • You escalate technical issues to product/engineering but own the customer relationship

Competitive Landscape

Main Competitors: Customer onboarding tools (UserGuiding, Appcues, WalkMe), workflow platforms (Monday, Asana adapted for onboarding), custom-built solutions

How They Differentiate: AI-powered features, purpose-built for B2B SaaS onboarding vs general workflow tools

Common Objections: "We already use [project management tool]", concerns about another system for customers to log into, ROI on specialized tool vs general platform

Win Themes: Likely faster time-to-value, better customer experience, data visibility into onboarding bottlenecks


What You'll Actually Do

Time Breakdown

Customer Meetings (35%) | Implementation/Support (30%) | Renewals/Expansion (20%) | Internal (15%)

Key Activities

  • Weekly/bi-weekly check-ins: You run calls with customer champions to review onboarding metrics, address blockers, and surface new use cases. Frequency depends on customer health and lifecycle stage.
  • Adoption work: You monitor product usage dashboards, identify customers not using key features, and proactively reach out to get them unstuck. A lot of time spent explaining workflows and best practices.
  • QBRs and renewals: You run quarterly business reviews showing ROI and prepare renewal conversations 60-90 days out. At this company size you likely own the full renewal negotiation.
  • Expansion hunting: You look for opportunities to expand to more teams, add seats, or upsell additional features. This means understanding customer org structure and building relationships beyond your main champion.

The Honest Reality

What's Hard

  • Customer champions leave or get busy - you spend time rebuilding relationships and getting new stakeholders up to speed
  • Implementation issues surface weeks or months after go-live when customers try to use advanced features. You're troubleshooting workflows you didn't design.
  • Early-stage product means features might not exist yet or have bugs. You manage customer expectations while advocating for fixes internally.
  • Small book means every churn hits your numbers hard. One churned logo can wreck your quarter.
  • Expansion requires you to be part account manager, part consultant - identifying pain points and building business cases while also being responsive support contact

What Success Looks Like

  • Net retention above 100% - your book grows through expansions even accounting for churn
  • Renewal rate above 90% (gross revenue retention)
  • Product adoption metrics up - customers using more features, logging in regularly, inviting more team members
  • Customers willing to be references, provide case studies, or introduce you to other teams

Who You're Selling To

Primary Buyers:

  • Customer Success / Onboarding leaders at B2B SaaS companies
  • Operations managers at client services organizations
  • Implementation directors at healthcare/logistics companies

What They Care About:

  • Time-to-value for their customers
  • Reducing manual onboarding work for their teams
  • Visibility into where customers get stuck
  • Customer satisfaction and retention metrics
  • Whether their customers will actually use another tool

Requirements

  • 2-4 years in customer success, account management, or implementation roles
  • Experience with B2B SaaS products, ideally in customer onboarding, engagement, or workflow tools
  • Comfortable managing renewal conversations and identifying expansion opportunities
  • Able to troubleshoot technical issues and explain complex workflows to non-technical users
  • Self-sufficient - at this company size you won't have layers of support
  • Willingness to work in an early-stage environment where processes are still being built