Head of Go-to-Market (GTM)

Head of Go-to-Market (GTM)

Full Time, Remote within US, with occasional travel in US

Professional Employer Organization (PEO) Broker Industry

PairPEO

The process of evaluating PEO’s can be a frustrating one - very manual with data collection, having multiple intermediaries, and inconsistent quotes from PEO providers. PairPEO is a 7-year-old PEO Broker & partner to companies going through the PEO evaluation process.

Our culture lives on the foundation of creating efficiency for our clients, PEO partners, and internal employees, with family first values. We work with a high sense of urgency while having fun, and providing excellent service and support to our clients.

Our Clients

Our clients save time & money, through the automation and price transparency involved in our evaluation of PEO options. This results in our clients securing a PEO that aligns with both their needs and their budget. Here at PairPEO we utilize our combined expertise in the PEO industry to issue an RFP on our client’s behalf, complete a side by side financial comparison of quotes, recommend the most appropriate partner, and assist through the onboarding & continued support. Our services are free to our client companies.

Head of Go-to-Market Role Overview

The Head of Go-to-Market will build & scale our growth engine. This role will be working in a remote environment, with no full time direct reports, interacting with external partners, and internal teammates on the Product, Development, Technology, and Marketing teams. Technical platforms include GoogleSuite, HubSpot, Apollo, and Slack among others.

This leader will own our GTM strategy across sales, events, marketing, partnerships, and revenue operations, focusing on growing employer demand, expanding strategic distribution channels, iterating on existing & new ICP’s.

This role is ideal for someone who is a strategic leader, a creative “builder,” results oriented, and has helped scale growth at a high-performing B2B, SaaS, or marketplace company, with a passion to create and expand demand generation engines.

Within your first 12-18 months, you will:

Build a Scalable Demand Engine

• Establish predictable pipeline generation across channel partners, direct inbound, events, and outbound programs
• Define clear ICP segments for companies evaluating PEO solutions
• Build a repeatable flow of qualified employers entering the PairPEO platform

Scale the Partner & Distribution Ecosystem

• Systematize how PairPEO recruits, enables, and activates channel partners and referral sources
• Increase partner-sourced opportunities as a percentage of overall deal flow
• Build playbooks that make PairPEO an easy and natural resource for partners advising clients on PEO decisions

Establish Market Category Leadership

• Position PairPEO as the default platform companies use when evaluating PEO solutions
• Increase brand awareness among business owners, CFOs, HR leaders, and advisors
• Build messaging & marketing that clearly communicates PairPEO’s differentiated platform approach

Operationalize the GTM Function

• Build the reporting, metrics, and systems needed to scale the revenue engine
• Establish clear visibility into pipeline performance, partner contribution, and conversion rates
• Align marketing, partnerships, and sales into a unified growth strategy

What you’ll need

• 8+ years experience in a B2B go-to-market leadership role across SaaS, marketplaces, or services-enabled technology businesses
• Demonstrated success building & scaling repeatable revenue systems, including demand generation, partnerships, and outbound pipeline creation
• Experience developing & managing partner-driven distribution models such as broker networks, consultants, referral partners, or strategic alliances
• Strong ability to move between strategy, systems, and execution, building structure while remaining hands-on
• Comfortable operating in early-stage environments where the playbook is still being written
• Experience translating complex service offerings into simple, scalable GTM motions

What’s nice to have

• Insurance brokerage distribution
• HR technology partnerships
• Benefits consulting firms
• Marketplace companies
• Channel-heavy SaaS businesses

What you’ll gain

• Autonomy from leadership to lean into your skill sets, knowledge, and experience to own & build this product line’s revenue strategy
• Base salary will depend on experience, and will be discussed in first round interviews
• Benefits including Medical, Dental, Vision, STD, LTD, 401k, PTO
• Be a part of a team that is highly emotionally intelligent, with a passion for high quality service and a family friendly culture.

Have questions or want an update on your application? Call or text Amanda @ 980.553.0103 or email Amanda@JoinBloomHR.com