16 ott - Milano
ShippyPro
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
Invii la sua candidatura dopo aver letto i requisiti di competenza e qualifica per questa posizione, riportati di seguito.
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. xkiyazw 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!
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