SMB Sales Team Lead – B2B SaaS

You know how to close deals. Now help a team close more of them.

You've spent 5+ years in B2B sales. You've hit your numbers, and you've already led people.

Now you want a role where you don't have to choose between selling and leading.

At ShippyPro, you'll lead our international SMB Sales team: around 5 people, and growing. This isn't a traditional management job, though. 40% of your time is selling. 60% is coaching, developing and leading.

You'll handle dozens of conversations and opportunities every week, and execution, follow-up and customer experience never slip.

If you like being close to customers, deals and your team, keep reading

About Us

Our mission is simple: Make People Work Better.

ShippyPro helps thousands of businesses across 30+ countries simplify and automate their shipping operations.

We're a top Shopify app in shipping and recognized by Gartner. Strong brand, strong product, real traction in the market.

We've raised $20M in total and we're ready to scale: a growing team, a marketing budget that keeps the pipeline full, and a Milan office that keeps getting bigger.

Our SMB segment is one of our strongest growth engines. It's international by nature, we acquire new customers every single day, and the sales cycle is fast.

The Product

ShippyPro is a shipping and fulfillment platform that helps merchants automate the entire shipping workflow, from choosing the best carrier service to generating labels and tracking deliveries. It connects with e-commerce platforms and multiple couriers, giving teams one place to ship faster, reduce manual work, and keep full control over costs and delivery performance.

The Challenge

We don't want structure that slows things down.

We want structure that makes speed repeatable.

Customers come in every day, from all over the world, and deals close fast. The challenge now is scale: more volume, more merchants, more markets. You'll bring the structure and the enthusiasm to make it all repeatable, without losing the energy that got us here.

Our customers expect fast answers, strong product knowledge and someone who quickly understands their business and helps them solve a real problem.

Every week, you'll manage a high volume of deals and conversations across:

Inbound. Outbound. Partnerships.

Your job is to keep that engine moving. Then help the entire team do it better.

Why ShippyPro?

You'll lead a growing international team and stay one of its most hands‑on sellers

You won't start from zero: marketing keeps the pipeline full, and new customers come in every day

You'll sell a product with a strong brand behind it, as a top Shopify shipping app recognized by Gartner

You'll work fast sales cycles with customers around the world, and see your impact week by week

You'll own a sales engine across inbound, outbound and partnerships

You'll shape how our SMB Sales organization scales: playbooks, hiring, onboarding

You'll have direct impact on one of ShippyPro's strongest growth engines

What You'll Do

Lead and develop our international SMB Sales team, spending ~40% of your time selling and ~60% coaching and leading

Personally own and close a high volume of SMB opportunities

Work side by side with the team on calls, demos, negotiations and deals

Coach the team through real opportunities and customer interactions, not theory

Improve conversion rates and sales velocity across the SMB funnel

Bring structure to a fast-moving engine: build and continuously improve repeatable sales playbooks

Review pipeline, performance and activity with the team

Step directly into important or difficult deals when needed

Hold an extremely high standard of customer care

Work closely with Marketing, Partnerships, Product and Customer teams

Help recruit and onboard new sales reps as the team grows

What You'll Bring

5+ years of experience in B2B Sales, with strong experience in B2B SaaS

Previous experience as a Sales Team Lead, Sales Lead or similar leadership role

A proven track record of personally hitting and exceeding sales targets

Strong experience selling to SMB customers

Experience managing high volumes of deals and customer conversations at the same time

Comfort working in a high‑velocity, high-performance sales environment

Strong organization, follow‑up and pipeline management

Experience coaching and developing other salespeople

Strong CRM discipline and the ability to work through data

Excellent English, which you'll use every day with customers around the world

High energy, ownership and a strong bias toward execution

Nice to have:

Experience with p