Senior Account Executive

Title: Senior Account Executive

Location: Hybrid (Portland, ME or Boston, MA preferred, open to remote for exceptional candidates)

Reporting Structure: Reports to Founders, David & Chris

Company Description

Our client, Trailmix Labs, is a fast-growing AI consulting and software company helping mid-market businesses modernize operations through AI-powered solutions, automation, and custom tooling.

They partner with legacy and operationally complex businesses to identify pain points and implement practical AI workflows that drive real business outcomes. Their work spans consulting, workflow modernization, custom software development, and AI-enabled operational transformation.

The team is deeply technical but highly pragmatic, using whatever tooling best solves the customer problem, whether that's Anthropic tooling, Vercel, Railway, Modal, or other modern AI infrastructure. They are intentionally tool-agnostic and customer-obsessed.

Quick Facts

• Founded by highly action-oriented and community-driven operators
• Profitable and grew from $0 to $1M ARR in under a year
• Currently 3 full-time employees plus a small network of highly specialized engineers
• Average ACV around $120K with strong expansion and renewal opportunities
• Customers are primarily mid-market, non-technical companies with $5M-$500M in revenue
• Fast-moving environment with extremely short sales cycles (often under 30 days)

This is an opportunity to join extremely early and play a foundational role in helping scale the company from $1M to $3M+ ARR.

Responsibilities

• Own the full sales cycle end-to-end, including prospecting, outbound outreach, discovery, proposal development, negotiation, close, renewals, and expansions
• Build and manage relationships directly with CEOs, CFOs, COOs, and other senior executives
• Generate new business through highly creative outbound strategies including networking, referrals, events, on-site meetings, cold outreach, and relationship-driven prospecting
• Identify operational inefficiencies and business pain points within legacy organizations and translate them into AI-driven solutions
• Work closely with founders and technical teams to shape customer solutions and sales strategy
• Drive approximately 2 new customer wins per month against a ~$2M annual quota
• Manage both inbound and outbound pipeline generation (roughly 50/50 split)
• Travel occasionally for customer meetings, relationship-building, and closing opportunities
• Help define and scale the company's go-to-market motion during a critical phase of growth
• Serve as a consultative advisor to customers around AI adoption, workflow modernization, and operational transformation

Qualifications

• Proven track record as a highly successful hunter Account Executive with demonstrated ability to source, prospect, and close net-new business independently
• Experience owning the entire sales process from prospecting through renewals and account expansion
• Strong executive presence and consultative selling skills with C-suite stakeholders
• Exceptional relationship-building and networking abilities with highly creative outbound instincts
• Demonstrated success hitting or exceeding aggressive quotas in fast-moving sales environments
• Entrepreneurial mindset with comfort operating in ambiguous, high-autonomy startup environments
• Strong curiosity and enthusiasm around AI, LLMs, automation tooling, and modern software workflows
• Ability to understand operational business challenges and position AI solutions in practical, value-driven ways
• Experience within high-growth SaaS, startup, or boutique consulting environments strongly preferred
• Experience helping scale revenue in early-stage or high-growth environments preferred
• Strong preference for candidates from startup, SaaS, or modern consulting organizations
• Based in or willing to spend some time in Portland or Boston preferred

Why This Role Is Exciting

• Extremely early-stage opportunity with meaningful ownership and influence
• Ability to work directly with founders in a highly collaborative environment
• Real autonomy to shape how sales and growth are built
• Fast sales cycles with strong customer demand and expansion potential
• Opportunity to sell highly relevant AI solutions into real operational business problems
• High-impact role with visibility across the entire company

Compensation & Benefits

• $130-160K Base Salary
• $130-160K Variable Compensation (OTE: $300K), flexible for the right candidate on salary
• Significant ownership and influence in a rapidly growing business
• Flexible and async-first culture
• Opportunity for meaningful career growth as the company scales

Interview Process

1. HigherPeople Recruiter Screen
2. Hiring Manager Interview
3. Prospecting & Discovery Assessment
4. Final On-Site Interview