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Sales & Onboarding Specialist
Remote, full-time, W-2. $80,000 to $120,000 total compensation.
Why Sentinel, why now
Sentinel launched on August 10, 2026. In under three months, more than 20 businesses have put their AI to work on their own Sentinel, and demand is now ahead of what one founder can demo.
- Industries: real estate investing, brokerage, restoration, plumbing, pool enclosures and beauty supply distribution
- AI tools supported: Claude, ChatGPT and Grok, all running on the same platform
Sentinel gives a business's AI its own workspace to build real tools: live dashboards, CRM connections, apps and automations. Owners get monitoring, snapshots and backups, so they can trust what their AI is doing.
Our growth comes from relationships and client referrals. Sentinel is now being set up as its own company, and this is one of its first hires. You get in on the ground floor, work directly with the founder, and help build the sales and onboarding playbook everyone after you will use.
The role
You own the client from the first demo to a live, working Sentinel, and you stay their account manager after that. One person, one relationship: the client never gets handed off between a salesperson and a setup team. You report directly to the founder, Laine.
Sales and account management
- Run discovery calls and demos for inbound leads and referrals.
- Find the prospect's most painful, specific problem and show how their AI solves it on Sentinel. The problem comes first; the platform follows.
- Follow up on every open deal and keep each prospect's notes, next steps and status current in our pipeline.
- Close new Sentinels and grow existing accounts through additional Sentinels, new users and referrals.
- Act as account manager after go-live: answer client questions, spot new use cases, and keep clients active and paying.
- Record your calls so they can be reviewed and used for coaching.
Onboarding
- Lead the onboarding call: connect the client's AI tool to their Sentinel, load their starter folder, and walk the AI through its first prompts.
- Get the client to a first real win on the call, such as a working answer from their own data.
- Guide clients to set up their own connections and enter their own credentials. Clients own their systems; you guide, you don't take over.
- Keep setup steps click-level simple and write clear prompts the client can paste into their AI.
- Check in during the first 30 days, unstick clients when they get stuck, and point them to templates and weekly Office Hours.
- Report onboarding friction back to the platform team so the next client goes faster.
What success looks like
Training takes three weeks. After that, you are demoing and onboarding on your own, and these are the goals we measure.
| By | Goal |
|---|---|
| Weeks 1 to 3 | Training. Learn Sentinel inside and out, shadow live demos and onboardings, and run practice demos with the founder. |
| Day 30 | Running your own demos and onboarding calls, with your first clients live on their Sentinel. |
| Day 60 | Managing your own pipeline end to end, with a steady weekly rhythm of demos, follow-ups and onboardings. |
| Day 90 | Closing new Sentinels every month, onboarding them, and growing those accounts, plus improving the playbook for the next hire. |
What you bring
- 2+ years in a client-facing role in B2B software sales, customer success, account management or onboarding.
- You use AI tools like Claude or ChatGPT every day and can explain them to someone who has never used them.
- Comfortable running live demos and screen-share setups with non-technical business owners.
- Clear, plain writing. You can turn a technical step into instructions anyone can follow.
- Organized follow-through. Nothing falls through the cracks.
Nice to have: experience working directly with business owners and decision-makers, and talking with them in terms of their results, time and money; familiarity with CRMs such as Salesforce, GoHighLevel or Housecall Pro; time at an early-stage startup where you built the process as you went.
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