HelloSky · 1 day ago
Customer Success Manager
United States
Contract
Remote
Mid LevelHelloSky is a venture-backed AI startup reinventing executive search and talent intelligence. They are seeking a hands-on Customer Success Manager to own post-sale outcomes and directly drive renewals and expansion, working closely with the VP of Sales and Product to deliver measurable customer outcomes.
Artificial Intelligence (AI)Human ResourcesMachine Learning
Hiring Manager
Mike Kelch
Responsibilities
Lead onboarding, training, and ongoing success for new customers and trials
Manage renewals proactively with a defined renewal calendar, forecasting, and executive-level communication
Identify and drive expansion opportunities (additional seats, higher tiers, add-ons) in partnership with Sales
Maintain rigorous usage tracking and customer health scoring to flag risk early and uncover growth opportunities
Run customer check-ins and QBRs for larger customers to drive outcomes and strengthen relationships
Iterate on simple playbooks: onboarding plans, success plans, QBR templates, renewal process, and risk mitigation
Partner with Product and Sales to translate customer feedback into actionable insights (bugs, requests, workflow improvements)
Help define the CS operating rhythm, metrics, and tooling as we scale
Qualification
Required
Experience supporting executive search / recruiting workflows or B2B SaaS Customer Success / Account Management with executive stakeholders
Proven ability to own outcomes: adoption, retention, and customer growth (renewals and/or expansion)
Strong communication, relationship management, and structured problem-solving skills
Comfortable in fast-moving startup environments—able to operate with ambiguity and build process as you go
Available for 20–40 hours/week with flexibility based on customer needs
Preferred
Executive search / retained search background
Quota-carrying renewals/expansion or revenue-target responsibility
Experience with HR tech, recruiting tech, AI/ML platforms, or talent intelligence tools
Familiarity with tools like HubSpot (or other CRMs), product analytics, and customer health scoring systems
Benefits
Meaningful equity upon conversion to full-time (early-stage upside)
Fully remote work with flexibility (with optional in-person meetups/offsites as available)
Collaborative team environment with clear operating rhythms and strong cross-functional partnership
Company
HelloSky
HelloSky offers an AI Talent and Company Intelligence Platform for executive and tech talent acquisition.
Founded in 2020
11-50 employees
Funding
Current Stage
Early StageTotal Funding
$8M2025-04-23Seed· $5.5M
2022-03-17Seed· $2.5M
2020-05-01Pre Seed
Recent News
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2025-09-03
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2025-05-07
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2025-04-26
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