Pear-VC

Account Executive (Mid-Market)

New York City
Full-time
$150K - $250K
Posted Oct 29, 2026

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Skills

Lead Generation
Negotiation
Operations
Sales

Job description

ACCOUNT EXECUTIVE (MID-MARKET)

New York City · Full-time · In person

COMPENSATION

$150,000–$225,000 annual on-target earnings (base salary + commission), plus meaningful equity.

ABOUT FRONTDESK

Frontdesk is building AI workers that run customer operations across voice, text, email, and chat. We are starting with the property management industry.

Our AI handles real work across the customer journey, from answering inbound calls to following up with leads, coordinating workflows, and taking action across the systems businesses already use.

We're growing quickly and moving upmarket. Over the last year, the size of the contracts we've been closing has grown roughly 10x, with several opportunities now reaching six figures and beyond. You're joining at an ideal stage: we've established repeatability and early playbooks, but they're still young enough for you to meaningfully shape how we scale them.

ABOUT THE ROLE

We're hiring a Mid-Market Account Executive to help build the next stage of our sales organization.

This is a true full-cycle role. You'll own prospecting, cold outreach, discovery, demos, follow-up, negotiation, and close.

You'll initially focus on mid-market customers, with most deals around $8K–$25K ACV. If you're consistently performing, you'll have the opportunity to move quickly into larger mid-market and enterprise accounts.

There are no territories. If you find a great account, go win it.

You'll have support from SDRs, marketing, founders, and the broader team, but you'll own your pipeline and your number.

KEY RESPONSIBILITIES

•Own your pipeline from first touch through signed contract.

•Prospect aggressively through cold calls, email, referrals, events, and creative outbound.

•Run discovery, product demonstrations, negotiations, and closing.

•Sell directly to owners, operators, and executive stakeholders.

•Multi-thread accounts and keep deals moving.

•Consistently meet and exceed sales targets.

•Bring customer feedback directly into Product and Engineering.

•Help shape our messaging, sales process, hiring bar, and team culture.

•Attend industry events and meet customers in person when it helps win.

WHY GREAT SALESPEOPLE SHOULD JOIN FRONTDESK

•You're joining an early sales team. You'll have a real influence on how the sales organization gets built.

•No territories. Great accounts are there for you to go after.

•Real ownership. We care about the outcome, not whether you followed a prescribed process.

•Increasing deal sizes. Start by mastering $8K–$25K deals, then earn your way into increasingly large accounts.

•Build the playbook. A lot of what our future sales team does will come from what you figure out now.

•Sell something customers actually care about. AI is fundamentally changing how businesses handle customer operations, and we're still early in that transition.

REQUIREMENTS

•At least 3 years of professional sales experience, including a quota-carrying B2B software Account Executive role and a track record of meeting or exceeding quota.

•Comfortable generating your own pipeline rather than relying entirely on inbound or SDRs.

•Strong cold calling, discovery, demo, negotiation, and closing skills.

•Competitive and highly accountable for your number.

•Excellent follow-up and pipeline management.

•Comfortable selling to both operators and executives.

•Able to learn a technical product quickly.

•Excited by an early-stage environment where the playbook is still being written.

•Based in New York City and able to work in person from our NYC office.

Preferred: experience selling to property managers, multifamily operators, or real estate businesses; previous BDR/SDR experience; and experience at an early-stage or similarly sized technology company.

WHY JOIN

You're joining early enough to actually shape the company.

This isn't a role where you'll inherit a territory, run someone else's playbook, and optimize around the edges. You'll help us figure out how Frontdesk sells, who we hire, how we compete, and what kind of sales culture we build.

If you're great, the scope will expand quickly.

Come help us build the sales organization you would have wanted to join.