VP of Sales

Compensation:

Competitive contract rate (DOE) + equity | Target conversion to full-time in ~60–90 days

About HelloSky

HelloSky is a venture-backed AI startup reinventing executive search and talent intelligence. We help leading executive search firms, private equity / venture capital teams, and corporate talent leaders source and engage the right people faster—using automation, high-quality data, and modern workflows. ( HelloSky )

We’re entering a new phase of growth and are hiring a hands-on Customer Success Manager to own post-sale outcomes and directly drive renewals and expansion.

Why This Role Matters

This is an individual contributor role at the intersection of customer success and revenue. You’ll own post-sale execution for a set of accounts—driving onboarding, adoption, renewals, and expansion. You’ll work closely with the VP of Sales and Product to deliver measurable customer outcomes and build lightweight, repeatable success motions as we scale.

What You’ll Do****Own the Customer Journey & Drive Revenue

• 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

What We’re Looking For****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

What We Offer

• Competitive contract rate with a clear path to full-time employment
• Meaningful equity upon conversion to full-time (early-stage upside)
• High-impact, high-ownership IC role with direct influence on renewals and expansion
• 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