Founding Account Executive (Full-Cycle Sales / Closer)

Founding Account Executive (Full-Cycle Sales / Closer)
Tobie | Early-Stage HR Tech / Benefits SaaS
We’re looking for someone who knows how to take a sales opportunity and finish it.
Tobie is building a benefits education and employee experience platform that helps companies turn complicated benefits information into something employees can actually understand and use.
The product is built. We’re selling. Now we need someone who can own opportunities from the first serious conversation through signed contract.
This is not an SDR role. We’re not looking for someone whose job ends when a meeting gets booked.
We want someone who can get on the call, understand the buyer, run discovery, demo the product, build the business case, handle objections, follow up relentlessly without being annoying, navigate HR/benefits buying processes, and ultimately ask for the signature.
What you'll own
Run discovery calls with HR, People, Benefits and executive buyers
Lead product demos
Understand the employer's current benefits communication problems
Build relationships with multiple stakeholders inside an organization
Create and manage proposals
Handle objections and competitive conversations
Keep deals moving when they start to stall
Navigate procurement, security and contracting conversations
Follow up consistently and intelligently
Negotiate and close
Own the opportunity until the contract is signed
Help us improve the sales process as we learn what works
Who we're looking for
You’ve closed B2B deals before.
Ideally, you understand some combination of:
HR technology
Employee benefits
Benefits communication
Insurance
SaaS
HRIS / HCM platforms
Selling into HR and People teams
More important than having the perfect resume is knowing how to move a real deal forward.
You should be comfortable working directly with the founders, operating without a giant sales organization behind you, and figuring things out when there isn't already a playbook.
We're especially interested in someone who has been a strong Account Executive, Enterprise AE, Benefits Consultant, Benefits Technology salesperson, or early-stage SaaS seller.
About Tobie
Employers spend an enormous amount of money on employee benefits, but employees are still often handed PDFs, emails and enrollment meetings and expected to figure everything out.
Tobie gives employees one place to understand their benefits, ask questions, see the source behind an answer, watch personalized content and actually understand what their employer is offering them.
We believe benefits is our entry point into a much larger HR technology opportunity.
We're early, we're moving fast, and we're looking for someone who wants to help us close the first wave of customers and build the sales machine with us.
If you’re the person people bring in when a deal actually needs to get across the finish line, I want to talk to you.

Work arrangement
Yes