SMB Sales Team Lead – B2B SaaS

ShippyPro; Lombardia; Hybrid; EUR 40,000 - 70,000; Full time

Benefits offered by this job

Meal vouchers

Mental health support

Learning budget

Hybrid Milan office

Flexible working policy

Home office allowance

Job summary

ShippyPro is hiring to lead its international SMB Sales team. You will split time between selling and coaching, and manage dozens of conversations weekly. You will drive speed, accuracy and customer focus across inbound, outbound and partnerships to scale our SMB pipeline.

The role leverages your 5+ years in B2B SaaS, proven leadership, and a passion for helping teams close more deals with speed and consistency. Milan-based, hybrid work setup.

Qualifications

• 5+ years in B2B SaaS sales or leadership roles.
• Proven track record of hitting and exceeding targets.
• Experience selling to SMB customers at scale.
• Experience coaching and developing other salespeople.
• Strong CRM discipline and data-driven approach.
• Excellent English with global customers.

Responsibilities

• Lead and develop the international SMB Sales team (~5 people).
• Split time ~40% selling and ~60% coaching/leading.
• Own and close a high volume of SMB opportunities.
• Collaborate with marketing, partnerships, product and customer teams.
• Improve conversion rates and sales velocity across SMB funnel.
• Build and update repeatable sales playbooks.
• Review pipeline and team performance regularly.
• Recruit and onboard new sales reps as the team grows.

Skills

B2B SaaS

Sales leadership

Sales targets

SMB sales

High-volume deals

CRM discipline

Coaching

English

Execution

Tools

HubSpot

Job description

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 partnership-generated opportunities
• An eCommerce or logistics SaaS background
• Experience with HubSpot or similar CRM platforms
• Experience selling across multiple international markets
• Additional languages

What Makes You a ShippyProer

• You lead from the front. You don't coach from the sidelines. You get into deals with the team.
• You love selling. Leadership hasn't taken you away from customers, calls and closing.
• You thrive on velocity. You handle many opportunities at once without sacrificing quality.
• You're a problem-solver. You work with customers & partners to solve real challenges fast.
• Your gift is in analysis. You can quickly grasp big ideas and measure how they impact revenue.
• You're a team player. It's who-you are, even when quick‑selling is in the paralipsis of the job.
• You lead the team from inside the action. You can quote just a chunk of time you do so.

Why Join Us

• Competitive salary between €40,000 and €50,000 (OTE €55,000-€70,000), calculated through our salary simulator - built on objective metrics, because we believe in unbiased compensation
• Meal vouchers (office or remote)
• Mental health support & fitness benefits
• Yearly learning budget and AI tools
• Flexible hybrid setup from our Milan office, with expenses-paid trips to HQ for team meetups
• No clock-in/out policy and one-time home office allowance
• Birthday Time Off – one extra day off, just for you!
• Career Growth Program - clear growth paths, structured goals, and continuous feedback
• An international team that moves fast and cares about building things well

Our Hiring Process

• Application review
• Intro call – 30 min with our People and Culture Team to align on expectations and context
• First interview – a deep-dive with our Sales Country Manager on how you sell and how you lead
• Practical sales case / role play - a hands-on exercise to see how you approach a real sales situation
• Final interview – meet the broader team and leadership

We move fast and keep things transparent.

We're not looking for someone who sees leadership as a way to move away from selling.

We're looking for someone who wants to lead the team from inside the action.

Someone who can handle the pace, close deals and make everyone around them better.

A Note Before You Apply

If you want to move on with the application, you'll have to answer a few questions. We love AI (it's part of almost everything we do!) so feel free to use it. But make sure your answers still sound like you.

Treat it like a first call: be real, be sharp, and give us a reason to book the next one.

Thanks for considering joining our team. We look forward to hearing from you!