Account Executive, Mid-Market

Maintruth; Northern (KY); Hybrid; USD 150,000 - 180,000; Full time

Benefits offered by this job

Medical coverage

Dental coverage

Vision coverage

Flexible time off

Remote first

Job summary

Maintruth, a remote, product-led security questionnaire startup, is hiring its first dedicated sales hire. You’ll own mid-market outbound, run full cycles, and craft demos that draft client questionnaires in minutes.

Sell to heads of security, GRC, and COOs, with OCPE on quizzes. Expect weeks-long cycles, frequent multi-stakeholder reviews, and a chance to shape our playbook and growth.

Qualifications

• Three+ years in B2B SaaS sales closing deals as a quota-carrying rep.
• Proven track record of hitting quota with deal-by-deal detail.
• You source your own pipeline and perform cold outreach.
• Able to discuss security posture with a technical buyer without a SE.
• Familiar with using AI to enhance sales workflows.
• Wants ownership in a fast-growing, early-stage startup.

Responsibilities

• Build your own pipeline through outbound into mid-market companies facing security reviews.
• Run the full sales cycle from first cold email to signed order form.
• Demo Maintruth on the prospect's questionnaire to showcase drafting in minutes.
• Multithread across security, revenue, and the executive team to keep deals moving.
• Keep pipeline and forecasts accurate in the CRM.
• Tell product what you hear on calls and influence the roadmap.
• Draft the initial sales playbook with sequences, talk tracks, and pricing discussions.

Skills

B2B SaaS sales

Quota attainment

Prospecting

Technical buyer conversations

AI in sales

Playbook development

Security/GRC sales

Job description

Maintruth answers buyer security questionnaires. Our customers upload their SOC 2 report, policies, and past questionnaires. Maintruth compiles those documents into a reviewed knowledge base, drafts every answer on the next questionnaire in minutes with citations, and writes the answers into the buyer’s original file.

Security reviews sit in the critical path of B2B revenue. Every enterprise deal our customers chase runs through one, and the questionnaire is usually the slowest step. That gives you a clean pitch. You’re selling deal velocity to people who are measured on it.

We’re a small, remote, product-led team. Customers can sign up on their own, run one questionnaire for $99, and grow into a monthly plan. You’d be our first dedicated sales hire, working directly with the founder.

The role

Mid-market companies get hit with security reviews from every direction. Enterprise prospects, procurement refreshes, and due-diligence processes all send questionnaires. These companies are big enough to face the volume and rarely staffed to absorb it. They’re your territory. You’ll sell to heads of security and GRC, to sales leaders whose deals stall in review, and to COOs who are still answering questionnaires themselves.

The motion is full cycle. Most of your pipeline will come from your own outbound, alongside inbound signups that look like they should be much bigger accounts. Demos are short and concrete. The prospect brings a questionnaire they’ve already suffered through, and Maintruth drafts it in front of them. Expect deal cycles measured in weeks, with security, revenue, and finance stakeholders in the room.

What you’ll do

• Build your own pipeline through outbound into mid-market companies that face a steady stream of security reviews.
• Run the full sales cycle, from the first cold email to the signed order form.
• Demo Maintruth on the prospect's own questionnaire, so they watch their last painful review get drafted in minutes.
• Multithread across security, revenue, and the executive team, and keep every deal moving with clear next steps.
• Keep pipeline and forecasts accurate in the CRM.
• Bring what you hear on calls back to the product, and help decide what we build next.
• Write the first version of the sales playbook, from sequences and talk tracks to pricing conversations.

What we’re looking for

• At least three years in B2B SaaS sales, including two or more years closing as a quota-carrying account executive.
• A record of hitting quota that you can walk us through deal by deal.
• You source your own pipeline and have the cold outreach to prove it.
• You can hold a conversation with a technical buyer about security posture without a sales engineer in the room.
• You already use AI in your own work. It's hard to sell an AI product convincingly if you don't.
• You want the early-stage trade. More ownership and a direct hand in the playbook, with fewer guardrails.

Nice to have

• You've sold security, compliance, or GRC products.
• You've run a named methodology like MEDDPICC and know which parts to keep.
• You've sold a product-led product, where the demo is a signup away.

What success looks like

• By the end of your first quarter, you've built pipeline from your own outbound, closed your first deals, and can run the whole demo without help.
• By the end of your second quarter, your motion is repeatable, your forecast holds up, and your playbook is something we could hand to the next rep.

Compensation and benefits

On-target earnings of $150,000 to $180,000 on a roughly even base and variable split, plus early equity at a stage where the grant is meaningful. We set the range from what comparable startups pay mid-market account executives, and we’ll walk you through how we landed on your offer.

• Medical, dental, and vision coverage.
• Flexible time off.
• Remote first. Work from anywhere in the US.

How to apply

Email [e-mail] with your resume or LinkedIn profile and a few sentences about a deal you’re proud of. Skip the cover letter. We read every application and reply to every one.

Maintruth is an equal opportunity employer. We evaluate candidates without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran status, or disability.

Send a short note about a deal you're proud of. We reply to every application.