Growth Marketing Lead: Trial Conversions
Job Title: Growth Marketing Lead: Trial Conversions
About Us
Prompt is revolutionizing healthcare with modern, automated B2B software for rehab therapy businesses, the teams within, and the patients they serve. We've become the go-to platform in the space, are setting a new standard in healthcare technology, and growing fast.
About the Role
We're looking for a Growth Marketing Lead to own the upsell trial motion for Prompt Plus, Sidekick, and Kiosk end-to-end, from first touch through paid conversion. This is geared towards current Prompt customers in a lifecycle/customer marketing style role. This role is equal parts architect and operator: you design the funnel, diagnose where it breaks, build the fix, ship it, and measure the result.
In this role, you'll partner closely with teammates across Product, Sales, Customer Success and Account Management, RevOps, and Creative teams. You'll set the strategy and execute on the plays, building repeatable trial-to-paid playbooks while raising the bar on activation, time-to-value, and conversion. Success is measured on trial activation, trial-to-paid conversion, and expansion revenue across Sidekick, Kiosk, and Prompt Plus.
Why Work for Prompt?
BIG Challenges: Here at Prompt, we are solving complex and unique problems that have plagued the healthcare industry since the dawn of time.
Talented People: Prompt didn't happen by chance, it's a team of incredibly talented and proven individuals who all made their mark before joining forces to build a transformational product.
Outcome-Oriented: We are outcome-oriented, data-driven, and focused on building the right things in the right ways at the right time.
Diverse Perspectives: We celebrate and leverage the diversity of thought and experience across the team to drive innovation and better solutions.
Customers: We are deeply passionate about improving outcomes in healthcare, and this passion pushes us to build something that practitioners genuinely love.
What You'll Do
Own the full trial funnel and execute hands-on. Own the trial journey from onboarding through activation through conversion to paid. Set monthly goals and drive improvements against key trial KPIs alongside CS and AM teams. This means you are in the tools daily, building onboarding sequences, writing the emails, configuring the Pendo guides, QA-ing the flows, and shipping the work yourself. You don't hand off a brief and wait; you build and launch. And think of creative ways to get in front of our target market.
Diagnose the funnel and prioritize what matters. Use product usage data, trial cohort performance, CRM signals, and qualitative feedback to identify the biggest drop-offs and prioritize the highest-impact fixes. Map the full trial experience from the customer's perspective, find where people get stuck or disengage, and turn those insights into a prioritized action plan. Also use this data to identify winback opportunities and re-engagement outreach for stalled or expired trials.
Run rapid experiments and optimize. Run structured tests across lifecycle messaging, in-product prompts, onboarding content, trial packaging, and assisted follow-up motions like sequences and collateral. You own the experiment from hypothesis through execution through measurement. Maintain a clear experiment backlog and a learning log so the team builds institutional knowledge, not just individual intuition.
Manage product updates and GTM for trial lines. Maintain product updates for Sidekick, Kiosk, and Prompt Plus. Plan GTM for each update including how it surfaces to net-new prospects along with customers, and manage update readiness and rollout. Translate product changes into updated trial messaging, onboarding flows, and enablement materials quickly. When a release ships, the trial experience should already reflect it.
Build trial enablement that the field actually uses. Create and maintain talk tracks, FAQs, objection handling, comparison guidance, and follow-up sequences that support assisted conversion. Partner with AM and Sales Enablement to make sure these materials are adopted and actually help close. Gather feedback from the field, iterate, and re-ship. You're writing these yourself, not briefing someone else to write them.
Bring creative energy to trial messaging. The trial inbox is crowded; the default onboarding email is ignored. Find fresh angles, test new formats like mailers, and push beyond standard lifecycle templates to create moments that actually get attention and drive action. Partner with Creative and Content to develop messaging that connects with busy practitioners.
Drive cross-functional execution. Partner with CS and AM to improve the trial experience and activation rates. Coordinate with Sales, RevOps, and Product on routing, handoffs, follow-up SLAs, and conversion blockers. When a handoff is broken or a follow-up SLA is being missed, you flag it, propose the fix, and drive it to resolution. You run the cross-functional motion, not just participate in it.
Build scalable trial plays and report on results. Build trial-to-paid plays by segment and use case, documenting what works and enabling consistent execution. Report on trial performance weekly: activation rates, conversion rates, time-to-value, cohort trends, and revenue impact. Use reporting to drive decisions, not just inform stakeholders. If the numbers say something isn't working, you're already testing the next approach.
What We're Looking For
5-8+ years in growth, lifecycle, or product marketing at a B2B SaaS company, with direct ownership of trial, freemium, or product-led growth motions
Proven track record of improving trial-to-paid conversion through hands-on funnel optimization, not just strategy decks. You've personally built the onboarding flows, written the emails, and configured the in-app messaging.
Deep experience with funnel diagnosis using product usage data, cohort analysis, and behavioral signals. You know how to find the drop-off, size the opportunity, and prioritize the fix.
Strong experimentation discipline. You've run structured A/B and multivariate tests across lifecycle channels and can show how those tests changed outcomes, not just produced learnings.
History of leading cross-functional execution with AM, CS, Sales, and RevOps. You've driven accountability across teams you don't manage and navigated competing priorities without losing momentum.
A creative mindset paired with execution speed. You're energized by finding new angles, testing bold ideas, and shipping them fast, not just brainstorming them.
Fluency in marketing automation, in-app messaging tools (Pendo or similar), and CRM platforms. You're a power user, not someone who needs a team to implement.
Excellent written communication. You can write a high-converting onboarding email, a sharp talk track, and a clear experiment brief without heavy creative support.
Bonus Points
Experience in health tech, healthcare SaaS, or outpatient therapy (PT, OT, SLP). You understand the practitioner persona, the workflows, and the language.
Experience with Pendo, HubSpot, or similar product analytics and CRM platforms
Background in product-led growth or hybrid PLG/sales-assisted models where you've had to balance self-serve conversion with human-assisted motions
Comfort building from scratch. You've stood up trial programs that didn't exist before, not just inherited and optimized mature funnels.
Track record of turning qualitative customer feedback into actionable product and messaging changes
Perks - What you can expect
Competitive salaries
Remote/hybrid environment
Potential equity compensation for outstanding performance
Flexible PTO
Company-wide sponsored lunches
Company paid disability and life insurance benefits
Company paid family and medical leave
Medical, dental, and vision insurance benefits
Discounted pet insurance
FSA/DCA and commuter benefits
401k
Complimentary subscription to digital fitness classes and wellness content
Recovery suite at HQ – includes a cold plunge, sauna, and shower
Here at Prompt, we are committed to fostering a fair and respectful work environment. As part of this commitment, it is our policy not to hire individuals from Prompt Customers unless they have obtained their current employer's explicit consent. We believe in upholding strong professional relationships and respecting the agreements and commitments our customers have with their employees. We appreciate your understanding and cooperation regarding this policy. Please don't hesitate to inquire with our team.
Prompt Therapy Solutions, Inc is an equal opportunity employer, indiscriminate of race, color, religion, ethnicity, ancestry, national origin, sex, gender, gender identity, sexual orientation, age, marital status, veteran status, disability, medical condition, or any other protected characteristic. We celebrate diversity and are committed to creating an inclusive environment for all employees
Prompt Therapy Solutions, Inc is an E-Verify Employer.