. Your job is to deeply understand how customers are using HelloSky, diagnose issues, proactively guide better search strategies, and help customers unlock more value over time. Renewals and expansion naturally follow—but your north star is customer success and search outcomes

, not account management.

What You’ll Do

Be a Trusted Search & AI Partner to Customers

• Act as a hands-on consultant for executive search firms and talent teams using HelloSky
• Help customers understand HelloSky filters and insights
• Coach customers on search strategy: filters, adjacencies, inclusion/exclusion logic, and iteration
• Guide customers toward better outcomes: stronger slates, faster time-to-shortlist, and higher signal

Obsess Over Usage, Outcomes, and Adoption

• Review customer usage data regularly to understand how HelloSky is actually being used
• Identify patterns that signal success, stagnation, or risk—and intervene early
• Proactively recommend workflows, saved searches, alerts, and strategies to increase value
• Turn “light users” into power users through targeted guidance and enablement

Drive Long-Term Customer Success (and Revenue as a Result)

• Own post-sale success for a portfolio of customers—from onboarding through renewal
• Lead onboarding and ongoing enablement with a focus on real search use cases
• Run structured customer check-ins and QBRs focused on outcomes, not vanity metrics
• Partner with Sales on renewals and expansions by anchoring conversations in demonstrated value

Be the Voice of the Customer Internally

• Surface product feedback grounded in real customer behavior and search workflows
• Partner with Product to improve usability, search relevance, and customer-facing features
• Help refine lightweight success playbooks, usage benchmarks, and customer health indicators

What We’re Looking For

Required

• Background in executive search, retained search, or senior recruiting

  , or

  deep experience supporting those users in B2B SaaS

• Strong intuition for how great searches are constructed—and why weak searches fail

• Comfort working directly with senior search consultants, partners, and investment professionals

• Analytical mindset: excited to look at usage data and turn it into action

• Attention to detail and data-driven methodologies

• Clear communicator who can coach, challenge, and guide customers constructively

• Comfortable operating in ambiguity at an early-stage startup

Preferred

• Former executive recruiter, search consultant, or research partner
• Experience with AI-powered search, talent intelligence, or sourcing platforms
• Exposure to renewals, expansion, or revenue responsibility tied to customer outcomes
• Familiarity with CRMs (HubSpot), product analytics, or customer health frameworks

What Success Looks Like

• Customers are searching more often, with better precision and confidence
• HelloSky becomes embedded in their daily search workflow
• Renewals are straightforward because value is obvious
• Expansion happens because customers want more—not because they’re pushed

What We Offer

• Competitive contract compensation with a clear path to full-time
• Meaningful early-stage equity upon full-time conversion
• Front line experience with AI adoption and enablement
• Rapid promotion opportunities
• Fully remote work with flexibility and optional team offsites
• Direct influence on product direction, customer strategy, and company growth
• The chance to truly unlock human capital and domain expertise at scale in the AI era