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Customer Success Manager

Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60601, USA
Listing for: HireBoost
Full Time, Remote/Work from Home position Listed on 2026-11-09
Job specializations:
  • Sales
    B2B Sales, Customer Success Management, Account Manager, SaaS Sales
Salary/Wage Range or Industry Benchmark: 3000 - 3500 USD Monthly USD 3000.00 3500.00 MONTH

Job Description & How to Apply Below

This is a remote position.

This company is the first and only all-in-one platform built to scale B2B go-to-market teams. It runs over 180+ live programs annually, featuring top thought leaders, practitioners, and founders in the B2B tech space. As a small but profitable organization moving at lightning speed, execution matters more than process, and the culture emphasizes collaboration, adaptability, and rolling up sleeves to figure things out together.
About the Role

We’re looking for a Customer Success Manager to own a book of 30–45 accounts at growth-stage B2B SaaS companies, with one clear goal: make sure every client gets real value and renews. You’ll lead onboarding, build relationships across each account (from frontline managers to economic buyers), deliver quarterly success plans, and own the renewal conversation end to end, including pricing and negotiation.

The focus is on account health and retention rather than upsell or expansion targets, and every account has an executive sponsor who partners with you on high-stakes conversations. This role is ideal for someone organized, AI-fluent, and confident engaging with VPs of Sales and CROs.

What You’ll Do

Onboard

  • Send a welcome email after signature, then run the kickoff call
  • Map the org and document the customer’s real goals
  • Send the 90-day learning path within 48 hours, with named people registered for sessions
  • Introduce and ramp up all relevant stakeholders and users

Build and hold the relationship map

  • Build and manage relationships with the key roles on every account
  • Keep proactive and reactive communication going year-round
  • Ask for introductions to new contacts and multi-thread every account, one of the highest-leverage parts of the role

Engage all year

  • Hold 3–6 substantive calls per account per year, depending on lifecycle stage
  • Build (using AI) and present a Mutual Success Plan, refreshed about every 90 days
  • Send dozens of one-to-one emails per week across your book
  • Connect with the economic buyer on every account every 90 days
Renew
  • Monitor account risk year-round and lead intervention plays when needed
  • Build and present the renewal case to decision makers and secure the renewal
  • Lead commercial conversations and price negotiations
Requirements
  • 3+ years in B2B SaaS customer success, owning renewals for a named book of accounts
  • Experience engaging revenue leaders (VPs of Sales, CROs, enablement leads) with confidence and well-informed opinions
  • Executive presence: clear, direct and concise communication, with strong rapport-building skills
  • Highly organized and system-driven, able to manage dozens of accounts, a rolling 90-day contact cadence, quarterly plan refreshes and a renewal calendar
  • Self-sufficient and comfortable working independently
  • AI fluency in the building sense, such as prompts, skills, agents or automations that others have adopted
  • Native-level written and spoken English
  • Availability for a full US business day on Central Time

Tools You’ll Use

  • Hub Spot as the system of record (experience required)
  • Google Workspace
  • Sybill for call recording and conversation intelligence (experience with Gong, Chorus or similar is a plus)
  • Claude, with a ready-made library of skills for account research, success plans, business reviews, session follow-ups and renewal prep
  • Atlas, an internal AI customer-success intelligence system that pulls together CRM, product usage, CSAT, call and public data on your accounts (training provided)
  • You’ll also build your own skills, prompts and automations. Deep technical skills aren’t required.
Benefits
  • Salary: $3000-$3500/Monthly
  • 100% Remote anywhere in LATAM
  • Holidays & PTO
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