Client Success Specialist, Tax Strategy

About HeyDrew

HeyDrew utilizes AI-powered tax strategies to minimize your business tax bill.

For decades, the ultra-wealthy have used the U.S. tax code to create, keep, and multiply their wealth. It’s not because they’re smarter or work harder. It’s because of one simple thing: access. Access to advisors who study the code year-round, finding every legal way to keep more of what their clients earn. The rest of us get a once-a-year appointment and a prayer.

HeyDrew is changing that. HeyDrew is a tax advisory firm that designs and delivers advanced tax strategies for the American entrepreneur. Our custom-built AI engine presents your specific tax-savings roadmap to a human tax professional, who will implement it alongside you. The best part: our team of Tax Valets will put your plan in place and help you maintain it all year long.

AI-Driven. Human Perfected.

About the Role

You’re the primary relationship owner for every HeyDrew client. Internally we call this role Tax Valet. Once a client signs, you own their entire experience from onboarding through strategy execution. You’re not a salesperson and you’re not a CPA. You’re the person who makes sure clients actually do what they came here to do.

You’ll run onboarding calls, guide clients through their AI-generated tax strategies, collect the documentation needed to execute, and hold clients accountable to deadlines. The CPA and EA team handles compliance review in the background. You’re the one talking to clients.

What you’ll own

• Onboarding: take the handoff from sales and run a two-call onboarding sequence. Call one covers orientation and strategy overview. Call two covers execution planning and task assignment.

• Client communication: you’re the client’s main point of contact for the duration of their program.

• Data collection: manage the full document collection lifecycle across onboarding and ongoing. Clients will not always upload what you ask on time. You know how to follow up, when to escalate, and how to keep things moving without losing the relationship.

• Strategy guidance: walk clients through their eligible strategies in real time using HeyDrew’s platform and AI support tools. You’re not giving tax advice. You’re helping clients understand what applies to them and what action they need to take.

• Task assignment and follow-through: assign action items, confirm next steps before every call ends, track progress per strategy.

• Escalation: know the boundary between what you can address and what belongs with the CPA or EA team. You don’t guess. You escalate.

What you bring

• Experience in a client-facing role where you owned the relationship: running calls, setting expectations, and being the main point of contact

• Comfort on the phone and on video, including following up with clients who are slow to respond

• Proactive and self-directed. You see what needs to happen and do it without waiting to be told

• Process-driven and detail-oriented. You follow a defined process, and when something is missing, you build or improve the checklist

• Ability to manage multiple active clients at once in a fast-changing environment

• Works well with a team and knows when to escalate to the CPA or EA team

• Comfort with CRMs and AI-powered tools in a live client setting (TaxDome, HubSpot, or similar)

• Onboarding, customer success, or startup and SaaS experience is a plus

• Experience in financial services, tax, or professional services is a plus, not a requirement. We train on the HeyDrew strategy framework and tools.

• Clear, direct communication. Warm but accountable

What this role is not

• Not a tax advisor role

• Not passive customer support

• Not a sales role

• Not task coordination without ownership

What Success Looks Like

Clients complete onboarding on time with their documents in order. They know what strategies they’re implementing, what they need to do, and when. They feel supported. They come back next year.