Director of Sales

Trellis (a ShipMonk Incubator Brand)

About Trellis

Trellis is a new, incubated business within ShipMonk, focused on modernizing transportation, carrier management, and shipping operations for small and mid-sized businesses. Just like a Trellis provides structure for plants to grow stronger and reach higher, we give merchants the backbone to scale their brands. In shipping, volume is the key to unlocking better rates and growth—but the merchants who need the most support are the ones who don't yet have the volume. That's why Trellis exists. Powered by a top domestic shipper, we have enterprise shipping solutions and pricing that we know would be the support structure you need to realize your brand's true potential. While Trellis is backed by ShipMonk’s scale, infrastructure, and credibility, it operates as a startup within a startup — building product, go-to-market, and customer value in its own ecosystem. This is a foundational sales leadership role, designed for someone who thrives in ambiguity, enjoys building from first principles, and wants direct influence over product, positioning, and strategy.

The Role

The Director of Sales will own Trellis’s go-to-market motion from the ground up. This person will be the first senior sales leader for Trellis, responsible not only for closing deals, but for shaping what Trellis sells, how it sells, and to whom. This role requires a founder mindset: someone who is equally comfortable selling, learning from customers, pressure-testing product assumptions, and partnering closely with the General Manager and Product team to build the business as we go. If being able to build something from scratch and truly own the outcome excites you, this is it.

What You’ll Do:

Build Sales from 0 1→ Personally drive early customer acquisition, acting as a player/coach. Leverage existing ShipMonk channels and resources, while building Trellis-specific channels

● Define initial ICPs, buyer personas, and use cases in partnership with GM and Product

● Translate early customer learnings into repeatable sales motions

● Interface with Pricing to drive profitability on new revenue

Shape Product & Strategy

● Help define Trellis’s value proposition, positioning, and ROI narrative as the product evolves through iterations with customers

Build the GTM Foundation

● Develop early sales processes, messaging, and qualification criteria

● Build any sales or marketing collateral needed

● Identify and pursue any key partnerships

● Establish CRM hygiene, forecasting discipline, and basic sales metrics

● Lay the groundwork for future sales hiring, enablement, and scale

Experience & Background

● Significant experience in the transportation, logistics, or supply chain industry, with

a deep understanding of last-mile carriers’ operations

● Proven success selling to an audience with a wide range of industry knowledge. From SMB founders with less transportation understanding to transportation leaders at enterprise-level businesses (e.g., Heads of Transportation, Logistics Managers)

● Experience selling complex, operationally driven solutions (not just SaaS shelfware)

● Prior experience in early-stage, build-as-you-go, or entrepreneurial environments strongly preferred

Mindset & Style

● Founder mentality: you take ownership, move fast, and figure things out

● Comfortable with ambiguity and evolving product definitions

● Hands-on, roll-up-your-sleeves approach — you like being in the deals

● Customer-obsessed and curious; you ask “why” often

● Collaborative, low-ego partner who works well across functions

● Able to operate with both strategic perspective and tactical execution

What Success Looks Like

In the first 6–12 months, you will have:

● Closed Trellis’s early lighthouse customers

● Helped define Trellis’s core ICPs and GTM strategy

● Influenced product direction based on real customer feedback

● Built a repeatable early sales motion

● Positioned Trellis to scale into a broader sales organization

● Influenced product direction based on real customer feedback

● Built a repeatable early sales motion

ShipMonk is an equal opportunity employer. We value diversity and do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.