Head of Support

Thoughtful is pioneering automation for healthcare providers. Our AI‑powered Revenue Cycle Automation platform helps the industry reclaim billions in lost revenue, accelerate payments, and free up staff for truly human work.

As Head of Support, you will architect, launch, and scale a world‑class, AI‑first global support organization that keeps our customers’ automated workforces healthy and productive 24 × 7 × 365. You will own the support strategy end‑to‑end—from defining the operating model and roadmap to building the processes, playbooks, and metrics that deliver an exceptional, “zero‑friction” customer experience.

This role demands a rare blend of strategic vision and tactical execution. You will be equally comfortable:

• Rolling up your sleeves to debug a stuck AI Worker in Python, or jump‑start a 2 a.m. incident bridge when revenue is on the line.
• Stepping back to architect a follow‑the‑sun support org and present an executive‑ready capacity plan for next quarter.

If you thrive on building and are obsessed with measurable outcomes, you’ll feel at home here.

• Set a bold vision for an AI‑powered support experience and translate it into a living roadmap of people, process, and platform investments.
• Build and coach a high‑performance global team of Support Engineers and Customer Success Analysts across LATAM and EMEA.
• Define and own support KPIs (e.g., ⩽ 6 h average ticket close time, ≥ 92 % SLA adherence) and continuously raise the bar through automation, analytics, and training.
• Partner cross‑functionally with Engineering, Product, and Customer Success to ship resilient features, coordinate incident response, and close the feedback loop.
• Turn data into insight using Zoho, QuickSight, Jira, and Google Sheets—surfacing trends that influence product roadmaps and customer outcomes.
• Champion the Voice of the Customer at every level of the company, ensuring product‑market fit tightens with every release.

Learn more about our Warrior culture and join us in redefining what “support” means in an AI‑driven world.

Own the Support Roadmap – Own the multi‑year vision, budget, and execution plan for a fast‑growing, AI‑centric support function.

Scale & Coach a Global Team – Hire, mentor, and inspire support staff in multiple time zones; create clear career ladders and performance frameworks.

Protect Uptime & SLAs – Monitor a growing army of AI Workers, lead blameless incident response, and keep average ticket close times ≤ 6 hours.

Deliver Data‑Driven Insight – Leverage Zoho, QuickSight, Jira, and in‑house dashboards to forecast demand, optimize staffing, and guide product priorities.

Champion the Voice of the Customer – Convert frontline feedback into actionable product and process improvements that drive retention and expansion.

Cross‑Functional Glue – Enforce a rigorous support‑handover process upstream: embed readiness criteria in every sprint, drive release checkpoints, and shepherd features smoothly into 24 / 7 operations.

• 8+ years leading technical support or customer success for SaaS or healthcare technology, including 3+ years operating a 24 / 7 global model.
• Proven track record scaling teams from <10 to 50+ while improving KPIs (response time, CSAT, cost per ticket).
• Deep expertise with ticketing/CRM ecosystems (HubSpot, Jira, Zendesk, or similar) and BI tooling (QuickSight, Looker, Google Sheets).
• Exceptional communicator able to brief C‑suite executives and frontline engineers with equal clarity and impact.

• Bachelor’s degree in a technical or quantitative field (e.g., Computer Science, Information Systems) or equivalent practical experience leading enterprise SaaS support organizations.
• Direct experience with Revenue Cycle Management, HIPAA‑regulated data, or healthcare payer/provider integrations.
• ITIL v4, PMP, or comparable service‑management certifications.
• Hands‑on history embedding AI/ML or RPA into support operations at scale.
• Proven experience supporting enterprise accounts that generate ≥ $1 M in ARR for your organization (customers typically exceeding $100 M in annual revenue).
• Experience managing offshore teams.

• Mission‑driven team reinventing how healthcare organizations operate.
• "Warrior" culture that values ownership, grit, and candor—read our manifesto.
• Competitive compensation, equity, and benefits.
• Unlimited opportunity to shape the future of AI‑powered operations.

Join us in redefining what “support” means in an AI‑driven world. Apply today.