Mid-Market Account Executive

Overview

You're selling Foley's all-in-one hiring, compliance, and background check platform to mid-market transportation, logistics, and field service companies (think trucking companies, waste management, utilities contractors). You handle the full sales cycle—prospecting, discovery, demo, negotiation, close. You're employee #1 in the Boston office, reporting into leadership but working somewhat autonomously to build your territory.

Role Snapshot

Company Context

Stage: Growth stage (344 employees, established product)

Size: 344 employees

Growth: Opening second regional office (Boston), expanding beyond original market

Market Position: Established player in transportation/logistics compliance—competing against legacy providers and point solutions

GTM Reality

Pipeline Sources:

• 30% Inbound - Website leads from companies searching for compliance solutions, some referrals from existing customers
• 60% Outbound - Cold calling HR/Safety directors, targeted LinkedIn outreach, industry event follow-ups
• 10% Partners - Some referrals from insurance brokers and industry consultants

SDR/AE Structure: No dedicated SDR in Boston initially—you're self-sourcing until the team scales

SE Support: Shared implementation/technical resource for larger deals, but you're running most demos solo

Competitive Landscape

Main Competitors: Legacy background check providers (HireRight, Checkr), niche transportation compliance tools, manual processes using spreadsheets

How They Differentiate: All-in-one platform vs point solutions, real-time compliance monitoring vs static background checks, industry-specific workflows for transportation

Common Objections: "We already have a background check vendor," price compared to basic screening, change management resistance from ops teams used to old processes

Win Themes: Consolidation (replacing 2-3 vendors), real-time monitoring catches issues before they become violations, ROI from avoiding DOT penalties and insurance claims

What You'll Actually Do

Time Breakdown

Prospecting (40%) | Active Deals (35%) | Internal/Admin (25%)

Key Activities

• Prospecting: 2-3 hours daily making cold calls to HR directors and safety managers at transportation companies with 100-500 employees. You're using LinkedIn Sales Navigator, industry databases, and some light account research. Goal is 8-10 conversations per day to book 4-5 discovery calls per week.
• Discovery & Demos: Running 45-minute discovery calls to understand their current compliance headaches (failed audits, driver turnover, manual tracking). Then scheduling 60-minute product demos showing how Foley tracks MVRs, drug tests, and certifications in one place. You're doing 3-4 of these per week.
• Deal Management: Chasing down multiple stakeholders (HR, Operations, Finance, sometimes Legal) to move deals forward. Lots of "following up" emails and calls because transportation companies aren't known for fast decision-making. Building business cases showing cost of non-compliance vs platform cost.
• Internal Coordination: Weekly forecast calls, getting implementation resources lined up for closing deals, working with marketing on territory-specific campaigns, documenting what's working in the Boston market for future hires.

The Honest Reality

What's Hard

• Transportation companies move slowly—lots of "we need to wait until after peak season" or "let's revisit next quarter." Your pipeline will slip constantly.
• You're competing against "good enough"—many prospects have a background check vendor and don't see the urgency to switch even if Foley is objectively better.
• First 6 months you're building everything from scratch—no warm leads, no local brand awareness, no established relationships. It's a grind.
• Compliance isn't sexy. You're not selling a product that makes people's jobs easier day-to-day—you're selling risk mitigation and regulatory coverage. The buying cycle reflects that (slow, committee-driven).
• You'll be somewhat on your own—founding Boston office sounds exciting but also means less support, fewer people to learn from locally, more ambiguity about what "good" looks like.

What Success Looks Like

• Closing 2-3 deals per quarter once you're ramped (Q1-Q2 is mostly pipeline building)
• Building a pipeline of 10-12 active opportunities at various stages
• Converting 25-30% of demos to closed deals within 90-120 days
• Establishing yourself as the go-to person for Northeast transportation/logistics accounts

Who You're Selling To

Primary Buyers:

• HR Directors at 100-500 person transportation companies
• Safety/Compliance Managers (often the end user)
• Operations VPs (control the budget)

What They Care About:

• Avoiding DOT violations and failed audits (expensive and reputation-damaging)
• Reducing time HR spends manually tracking driver certifications and background checks
• Insurance costs—carriers want proof of ongoing monitoring, not just hire-date checks
• Turnover—they need to onboard drivers fast, but can't skip compliance steps

Requirements

• 3-5 years full-cycle AE experience, preferably selling to operations or HR buyers
• Proven track record in SMB or Mid-Market SaaS ($25-100K ACV deals)
• Comfortable with outbound prospecting—you'll be self-sourcing most of your pipeline
• Experience navigating multi-stakeholder deals (HR + Ops + Finance)
• Willingness to work hybrid in Boston office (they're building local presence, expect 3 days/week in office)
• Grit—this isn't a role with a massive inbound lead flow, you're hunting and building from zero