Onboarding & Customer Success Specialist

We run a rolling advisory program for expert women building "microfirms" — lean, high-ticket consulting practices built around their own expertise — no fixed cohorts, new members enter every week. But the program isn't the product. The product is a proprietary software platform every member runs their business on. And right now, too many members aren't opening it. That's the job. We're not hiring an administrative onboarder to send welcome emails and check boxes. We're hiring someone who thinks like a SaaS onboarding or customer success person: how do you get someone from "I paid for this" to "I use this every day"? How do you spot the person who logged in once and never came back, before it becomes a churn problem? How do you turn a rolling wave of new signups into a rolling wave of active, engaged users? You'll still own the logistics layer — calendar, scheduling, first point of contact. But the reason this role exists is adoption. If someone leaves this program without the platform becoming part of how they run their business day-to-day, we've failed, regardless of how smooth their welcome sequence was. Here's why this is open now: we're enrolling 3–5 new members a week, and the founder is still the one doing onboarding, calendar management, and logistics by hand for each of them. This role exists to take that off her plate entirely, not to lighten the load a little. You'll report directly to the founder. This role consolidates onboarding, calendar, and liaison responsibilities currently being restructured — you'll have process documentation to start from, with the founder available to clarify priorities directly in your first few weeks. Who We Serve Our members are accomplished women, many exiting or already out of corporate leadership (VP, Director, C-suite, functional experts), who are building microfirms: one-to-few-person advisory or consulting practices that monetize deep expertise, serving service-based businesses often scaling toward the $1–2M range. Some walk in with a business already running and need real systems under it. Others are brand new to entrepreneurship and need the whole infrastructure. What they share is deep subject-matter expertise and no operational backbone yet to turn that expertise into a scalable, high-ticket practice. Our Mission We build the infrastructure that allows exceptional operators to build independent, enduring firms. What You'll Own Platform Adoption & Activation Own the new member's path from signup to active, habitual use of the platform — not just account setup, but actually opening it and working inside it Track activation and usage, not just task completion: who's logged in, who's stalled, who's quietly disengaging before they say a word about it Reach out directly to re-engage anyone drifting, the way a CS team would flag an at-risk account Feed friction points back to the team as product gaps, not just support tickets — if three people get stuck in the same place, that's a system problem, not a coincidence Enablement Content Build the content that gets people unstuck and back in the platform: short product walkthroughs, how-to guides, and a living wiki members can self-serve from Turn the same question you've answered three times into a piece of content, so the fourth person never has to ask Prioritize whatever content will move the current stalled or disengaged members, not a general content calendar — this is reactivation content, built in response to real drop-off, not evergreen marketing Keep it lightweight: a Loom-style walkthrough or a clear wiki page beats a polished production every time Member Onboarding Send welcome materials and orientation sequences as new members enter the program Set up member access across our platform, Slack, and Tally Be the first point of contact for new members navigating their first 1–2 weeks Calendar & Program Logistics Build and maintain the program calendar: live sessions, Orientation Days, recurring touchpoints Schedule calls and sessions as needed Keep calendar info synced and accurate across the tools members actually use Liaison Duties Be the go-to for logistics, scheduling, and "where do I find X" questions Route coaching, content, or strategy questions to the right team member — this is not a coaching role Flag repeat questions and friction points back to the team so we fix the root cause Light Automation Maintenance Update existing Zapier automations as workflows change (already built — this is maintenance, not building from scratch) Estimated ~1 hour/week; flag anything broken rather than troubleshooting deeply What Makes Someone Right for This You've onboarded users into a piece of software before — ideally something high-ticket or high-touch, where getting someone to actually adopt the tool mattered as much as getting them signed up. You know the difference between "set up" and "actually using it." You think in terms of activation, time-to-value, and engagement — not just checklists You can turn a repeated question into a simple walkthrough or wiki page without hand-holding — you don't need to be a content creator, but you need to be able to explain something clearly in writing or on screen Bonus if you've also supported a coaching program, course, membership, or cohort-based business. If you've done both software onboarding and program/community onboarding, you're exactly who we're looking for You notice when something's about to fall through the cracks before anyone has to ask You're comfortable with real autonomy — you'll have documentation to start from, but you're expected to use judgment, flag gaps, and improve the system rather than wait for direction You communicate clearly and warmly in writing — members form their first impression of this program through you You're comfortable with Slack, Google Calendar, and Zapier (or can ramp quickly); experience with GoHighLevel, Lovable, and Tally is a plus You can hold a boundary — you know exactly when something's a logistics question you handle versus a coaching question you route elsewhere You've worked in lean, founder-led businesses before — you know how to be the system, not just follow one This starts as a contractor role, with a clear path to full-time as we scale. What This Role Is Not This is not a sales, marketing, or brand content role — the content you create is functional (walkthroughs, wikis, help docs), not promotional. It's not a coaching role — you won't be advising members on their business strategy. It's not a full automation build — the Zapier infrastructure already exists; you're maintaining it. And it's not a pure administrative onboarding role — the metric that matters most here is whether members actually use the product. To Apply Tell us about a time you helped someone adopt a piece of software they were slow to actually use — what did you notice, and what did you do to get them across the line? If you have a second example from onboarding people into a program, course, or membership, include that too. Keep it brief; we care more about how you think about adoption and member experience than a polished cover letter.