SalesTechStar Interview With Jonnie Cartmill, Chief Sales Officer at Sendcloud

Jonnie Cartmill, Chief Sales Officer at Sendcloud expresses a few thoughts on today’s B2B sales dynamics and salestech tips that can drive better business output:


Welcome to this SalesTechStar chat Jonnie, tell us about yourself and more about being CSO at Sendcloud…

Thanks for having me! I’ve been with Sendcloud for almost three years now and took over the reins as Chief Sales Officer at the beginning of 2022.

I’ve been involved in SaaS sales for almost 15 years and started my journey at a bootstrapped scaleup called Meltwater. After seeing the company scale from a couple of 100 in 2008 to over 2500 people in 2019, and growing it from 50M ARR to half a billion, I felt it was time for a new challenge.

At Sendcloud I got the opportunity to build the sales foundation for one of the fastest-growing tech scale-ups in Europe, scaling the company from about 100 employees in 2020 to almost 500 today. Together with a team of over 150 sales professionals, across sales, customer success, and partnerships, we will grow Sendcloud to a $100M+ ARR machine. Our mission is to turn shipping from a bottleneck into an accelerator for growth!

As a seasoned sales leader: what would you say helped build the foundation of a strong sales success model?

When I first joined Sendcloud in 2020, there was a team of about 100 people, 20 of them in sales. However, there were already some ambitious plans to scale the team to around 100 sales professionals. Consequently, one of the first things I wanted to achieve was to develop the right organisational structure for scale, that could live, breathe, and grow into our longer-term company objectives.

At the time, the sales team consisted of 20 people divided into small sales teams focusing on separate markets. There was a mixture of specialization and full-sales cycle, and what was happening in the Benelux didn’t necessarily happen in the DACH region. Every market had its own structure, which made it hard to scale.

To build the right foundation for growth, we eventually tested both specialization and full-sales cycle as well as a hybrid model. In the end, the full-sales cycle proved to work best for us. By having one sales professional guide a customer’s purchase process from A to Z, this model makes it super easy to purchase our platform and removes the friction of a handover. As a result, our MRR increased, while churn decreased in this model.

Implementing the full-sales cycle not only improved unit economics but also helped create a competitive company culture. By giving sales executives the chance to manage the entire sales cycle rather than a small stage, we are able to promote competitive career paths, instead of just ‘sales jobs’. I believe a company’s success is built upon its people, business and culture.

People are our number one asset, and so creating clear career paths stimulating personal development, is key to fueling long-term business growth.

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We’d love to dive into your core sales models/strategies closer home at Sendcloud and a little about the salestech that helps drive your processes?

Sales tech should be an enabler for growth.

We evaluate our tooling based on

1) will this make our team more efficient with their time?

2) will it help our team to be better at what they do?

3) will it provide the ROI we expect as a company to justify the investment. With so much tech available, it’s important to use the right tools to get the outcomes you need for your business. The CRM’s we use include HubSpot (Sales), Gainsight (Customer Success), and PartnerStack (Partnerships).

We use Tableau to centralize all of this data visualization into a single-source of truth so that we can make informed decisions on rep, manager, and executive-level. As mentioned, personal development is core to our cultural values and business outcomes, so we also invest in tools like Jiminny (call recording and analysis) to enable reps and leaders to improve their methodologies, and Lessonly (learning management) to test and transfer knowledge with ease.

When it comes to B2B sales today, what do you feel sales people need to be doing more of to boost their ROI?

In my opinion, success in sales is not just about what you can do more of. Rather it’s about ensuring you are doing enough of the right things, in the right way, at the right time, to increase your chance of success. As a leader, it’s important to measure what you manage, and to guide your team towards success. Therefore, I’m a firm believer in data-driven management. Data helps us to make informed decisions, keeps our customers top of mind, and allows us to transfer knowledge to increase sales success.

That’s why at Sendcloud we’ve built a detailed but simple sales velocity calculator to reverse engineer success for our new business teams at rep, team, and global-level. If you understand exactly what you need to do to achieve your target, then you can manage your time appropriately. And, if you know what our ideal customer looks like and how to target them, it’s easier to close a lead. By offering our sales executives insights into our key success factors, we can create ownership and accountability which in turn increases efficiency.

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When it comes to creating a strong online sales/online buying experience: how can B2B sales teams work more closely with their marketing counterparts to build better journeys?

At Sendcloud we believe in leading by context rather than control. This means giving our people all the information needed to make the right call by themselves. When our people understand what it is we are doing, why we are doing it and where we are going, they will naturally know how to get there. As a result, leading by context results in more creative freedom, ownership and efficiency.

A prerequisite for leading by context is that we are all on the same page. To make sure we are all playing the same game, we have translated our mission into clear, company-wide annual goals. Because we all work towards the same overarching goals, marketing and sales naturally work together more closely. At the end of the day, they are both responsible for our mission to turn shipping into an accelerator for growth. A common goal therefore automatically leads to more collaboration between sales and marketing and consequently an improved buying experience!

Besides which, how can delivery centric businesses (Uber Eats and such others) also capitalize on creating improved customer experiences or rather, how they are already doing this with features like same-day delivery?

According to research we conducted among more than 7,500 consumers in Europe, 71% of consumers consider flexibility an essential element of delivery. Nowadays consumers want to decide for themselves when, where, and how to receive an order. A mix of shipping options, such as green delivery, same-day delivery, flash delivery or even locker delivery, is therefore essential to winning over the hearts of customers. Offering flexibility is therefore the only answer to improving the customer experience for the consumers of the future.

Some last thoughts, takeaways, on the future of sales and sales tech?

Buyers are better informed than ever before. With the rise of social media, review sites, and automation software, it’s important to separate yourself (as a sales person) from all of the noise. I believe that outreach automation will need to evolve, buyers are tired of being put into basic email cadences. Therefore, personalisation is key.

I’m a firm believer that people buy people; technology should be used to help you, but it shouldn’t replace the human touch. Nothing will beat a quality conversation with a prospective client over the phone, or in a face-to-face meeting. The last person that cold-called me, with the right approach, closed a deal 🙂

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Sendcloud is an all-in-one shipping platform that accelerates international growth. Sendcloud helps online retailers to save time on shipping and at the same time increase conversion by optimizing their checkout, offering branded tracking and a seamless return process for both businesses and consumers.

Jonnie Cartmill is the Chief Sales Officer at Sendcloud.

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ARRAutomation softwareB2B salesBusiness GrowthChief Sales Officercustomer experienceDACH regiondata-driven managementGainsighthubspotinterviewslocker deliveryMRROnline RetailersPartnerStackreview sitessales success modelSales TeamsSales TechSame-Day DeliverySendcloud