Vice President of Sales

Title

Vice President of Sales — Voicegain Casey (AI Voice Agents and Co-Pilots for Healthcare Payers)

Location

Remote (US) — preference for candidates in NY/NJ, Boston, or major Healthcare Payer hubs

Travel

33–50% (customer meetings, industry events, partner offsites)

Employment

Full-time, exempt

About Voicegain

Voicegain is a Voice AI company that offers two main products a) a Voice AI platform for builders of Voice-enabled Apps and 2) Voicegain Casey – purpose-built AI Voice Agents and Co-Pilots for Healthcare Payers. This position is to drive sales and market adoption for Voicegain Casey.

Voicegain Casey automates augments and analyzes inbound and outbound customer service phone calls for Health Plans, TPAs, Utilization Management providers, PBMs, and Telehealth organizations. Casey already processes over a million calls per year for a dozen payers while the underlying Voicegain platform processes more than three billion minutes of audio annually. You can learn more and also experience the product by clicking on this link.

We are a HIPAA, SOC 2 Type 2, and PCI-DSS compliant platform, and we are pre-integrated with the leading CCaaS platforms our customers use every day — Five9, NICE, RingCentral, Aircall, and Dialpad. With our recent acquisition of TrampolineAI, we are delivering an end-to-end Contact Center AI suite for healthcare payers that drives measurable outcomes: 25–50% reduction in OpEx, 10–15% lift in CSAT and NPS, and 3–5 minutes saved per call.

The Opportunity

We are hiring a Vice President of Sales to own the go-to-market for Casey across the U.S. healthcare payer market. This is a builder role — you will inherit a strong product, marquee logos, and clear category traction, and you will shape the sales motion, team, and pipeline that take Casey from early traction to category leadership.

You will be the senior commercial leader for the Casey product line: setting strategy, closing the largest deals personally, and recruiting the AEs, SEs, and SDRs who will scale the business behind you. You will work directly with the CEO, product leadership, and our customer success team to turn enterprise pilots into multi-year, multi-million-dollar payer relationships.

What you will own

Revenue and Pipeline

•   Own the annual new-logo and expansion ARR target for Casey across Health Plans, TPAs, UM/CM providers, and PBMs.

•   Personally lead the largest, most strategic enterprise opportunities — owning executive relationships at VP, SVP, and C-level (CIO, COO, Chief Customer Experience Officer, VP Customer Service).

•   Build a predictable, multi-quarter pipeline with clear stage definitions, accurate forecasting, and disciplined deal qualification (MEDDPICC, Miller Heiman or similar).

•   Partner with marketing to convert demand into pipeline through ABM, conferences (AHIP, RISE, HLTH), executive roundtables, and analyst engagement.

Team Building and Leadership

•   Recruit, hire, and develop a high-performing sales team — Enterprise AEs with healthcare payer experience, Sales Engineers fluent in CCaaS and contact center workflows, and SDRs targeting payer ICPs.

•   Establish the playbook: territory design, comp plans, ramp expectations, deal review cadence, and quarterly business reviews.

•   Coach the team in the field — joining customer calls, sharpening deal strategy, and modeling executive selling.

Go To Market Strategy

•   Refine the ICP and segmentation across regional Blues, national payers, TPAs, PBMs, and UM/CM specialists, and align resources accordingly.

•   Define and evolve the value narrative around the “buy vs. build” advantage of Casey: faster time-to-value (2–3 weeks vs. 3–6 months), production-grade LLM guardrails, integrated Co-Pilot, embedded voice analytics, and per-call economics.

•   Build and manage a partner ecosystem — CCaaS vendors (Five9, NICE, RingCentral, Dialpad, Aircall), CRM/EMR partners, and SI/consulting firms serving the payer market.

•   Work with Product on packaging, pricing, and pilot-to-production conversion strategy for the Fully Automated and Partially Automated call mix.

Cross Functional Leadership

•   Be the voice of the customer in product and engineering planning — surfacing payer-specific intents, integration requirements, and compliance needs.

•   Partner with Customer Success and Implementation to ensure smooth handoff from sale to pilot to scale, protecting Net Revenue Retention.

•   Operate the sales engine on modern tooling (Hubspot, Apollo, Clay) with clean data and clear KPIs reported to the CEO and board.

What you will bring

•   10+ years of enterprise B2B SaaS sales experience, with 5+ years in a leadership role (Sales Director, RVP, or VP Sales) carrying and exceeding multi-million-dollar quotas.

•   Deep familiarity with the U.S. healthcare payer ecosystem — Health Plans, TPAs, PBMs, UM/CM organizations — and the buying centers within them (Operations, Member/Provider Services, IT/Digital, Compliance).

•   Demonstrated experience selling at least one of: AI/ML SaaS, Contact Center / CCaaS, Conversational AI / Voice AI, healthcare technology, or enterprise contact center analytics.

•   Track record of building and scaling a sales team from early stage (sub-$10M ARR) toward category leadership.

•   Experience selling six- and seven-figure enterprise deals with 6–12+ month sales cycles, multiple stakeholders, and procurement, security, and compliance reviews (HIPAA, SOC 2).

•   Strong command of modern sales operating systems — pipeline hygiene, accurate forecasting, deal inspection, and data-driven coaching.

What you will get

•   Prior experience selling into mid-market Health Plans like the Regional Blues, Intermountain Health, Ascension etc. or experience selling into either large enterprise Health Plans like UnitedHealth, Centene, Cigna, Anthem/Elevance and Aetna.

•   Background in CX Software or any software that is sold to the Operations leadership in Payer organizations

•   Prior experience at a high-growth, founder-led startup as the first or second sales leader.

Preferred

•   A category-creating product with marquee payer logos and 1M+ live production calls behind it.

•   Direct partnership with a technical, customer-obsessed founding team.

•   Competitive base salary with uncapped variable compensation and meaningful equity in a healthcare AI company at an inflection point.

•   Comprehensive health, dental, vision, and 401(k) benefits.

•   Remote-first culture with budget for travel to customers, conferences, and team offsites.