Head of Inside Sales - CO, MA, OH, GA at SumUp (Greater Boston Area, MA)

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Sr. Director of Inside Sales -OR- Head of Inside Sales

Fivestars by Sumup is redefining the way businesses and communities interact by turning every business transaction into a customer relationship. As a leader in the SMB Loyalty & CRM space, Fivestars by Sumup is helping local businesses come back stronger than ever by turning their credit card readers into an all-in-one payments & automated marketing platform. Since launching in 2011, Fivestars by Sumup has become a robust national commerce network of over 70 million users engaging with thousands of small businesses resulting in $3 billion+ in local merchant sales annually. More than 1 million people sign up monthly to support the local businesses that make our neighborhoods great!!

In Oct 2021, Fivestars was acquired by SumUp – a financial technology company that allows businesses of all sizes to receive payments quickly and simply, both in-store and online. Named as Europe’s fastest-growing company in the Inc. 5000, SumUp supports over 3 million merchants globally and operates in 34 markets across Europe, the U.S., Brazil and Chile. With its card terminals and online services relied upon by businesses of all sizes from DHL to black cab drivers – SumUp is the partner of choice for small businesses from every walk of life.

We are seeking a high energy, passionate, results driven Head of Inside Sales for our growing Small & Midsize Business (SMB) Inside Sales and SDR organizations. This role reports to the SVP of Sales and is a key member of the Sales Senior Leadership team and will be responsible for managing the entire inside sales organization. You are a leader who finds true joy in helping others reach their maximum potential, and owns a "People First" mentality. The ability to have fun and become part of the team while leading is a must.

The role:

You will work directly with the SVP Sales to drive the growth and scale of our SDR and Inside Sales teams. As the Head of Inside Sales you will serve as the overall strategy and process leader for the Inside Sales organization and are accountable for the organization’s performance and scale. As a passionate sales professional you are hands on and enjoy directly engaging, leading, and developing high-performing teams. You bring with you experience working in a sales organization with the focus on small business sales and have a demonstrable track record of success as a leader of leaders in a scaling environment. You enjoy operating in a dynamic, transparent, and supportive setting.


  • Provide leadership for the day-to-day operations of Inside Sales and SDR sales organizations
  • Amplify a culture where coaching, mentorship, tools, and training are used to create a best in class inside sales organization with well ramped, trained and engaged sales reps and leaders
  • Measure the performance of the Inside and SDR sales teams, and use the measurement to both drive performance and support, mentor, and develop the teams and their leadership.
  • Lead, in partnership with Revenue Ops, the design and implementation of appropriate reports, metrics, and forecasting
  • Lead the direction and strategy on Insides Sales and SDR processes, programs, and skills attainment that will engage and retain top talent.
  • Collaborate with the Sales Learning & Development team to rebuild the new hire curriculum and create a plan to continuously level-up the teams and their leaders.
  • Develop and implement career path programs in Inside Sales and SDR teams and leaders. 
  • Experience planning, implementing, and communicating change
  • Ampliphy compliance with key sales tools such as Salesforce.com, Gong, and Outreach to continuously improve the impact of our sales efforts
  • Work well cross-functionally and own as your own your cross-functional leaders’ priorities when they involve your teams and leaders engagement
  • Create a great place to work by living out the SumUp values of Share Humility, Authentic Relationships, Warrior Spirit & Joy Every day.
  • Have never ending energy and optimism


  • 10+ years’ experience in inside sales including successfully leading and developing an inside SMB organization
  • Experience with scaling Inside Sales and SDR teams in fast moving environments
  • Experience leading leaders
  • Demonstrated Team quota achievement
  • Demonstrated success of training and coaching of new sales hires
  • Highly developed communication skills for all levels of an organization
  • Proven track record of driving discipline and rigor in the sales processes and engagement with sales tools
  • Ability to communicate, present and influence all levels both externally and internally, including executive and C-level
  • Motivating personality, personable, and magical ability to connect with salespeople and business owners
  • High level of integrity, customer service, and customer management skills
  • Excellent verbal, written, and presentation skills

Job Application Tip

We recognise that candidates feel they need to meet 100% of the job criteria in order to apply for a job. Please note that this is only a guide. If you don’t tick every box, it’s ok too because it means you have room to learn and develop your career at SumUp.

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Boston, MA

An Insider's view of SumUp

What’s the vibe like in the office?

Our SumUp Boulder office is full of collaboration! We work in an open environment and our team is cross-functional. SumUp is constantly growing and while being on this amazing journey we just enjoy learning from each other!


Business Operations Manager

What does your typical day look like?

I start most morning catching up on Slack messages and emails with a cup of coffee. Then I pick up what I was working on the previous day. After my team’s standup, I make some food and take my lunch break. Most of my meetings happen in the AM, so I usually get undisturbed focus time for the rest of the workday.


Software Engineer

What makes someone successful on your team?

What I love about sales is that you can learn a repeatable process that works and you can still give it your own personal touch. The most successful people understand this and quickly focus on learning and owning this process, so they can put it into practice a lot more often!

Jean Marco

Outside Sales Regional Manager

What are some social events your company does?

One of our core values at SumUp is “We care” — and this applies not just to our customers, but also to each other. The pandemic has made it hard to spend time together as a team, but whether it’s a quarterly town hall or remote team breakfasts, carving out time for (safe, socially distanced) team events has really helped keep our team connected.


Managing Director

What are SumUp Perks + Benefits

SumUp Benefits Overview

SumUp is located on Pearl Street in downtown Boulder. Beyond the beautiful views of the Flatirons from our office we offer:

- Health, dental, vision and life insurance
- FSA & 401k retirement plans
- Immediately available PTO
- Startup vibes + cross-functional teams
- Weekly team events and milestone celebrations
- A rotating selection of free beer
- Free EcoPass for public transport all around Colorado
- One Outdoor/Powder Day a year! This is why we work in Boulder right?

Friends outside of work
Eat lunch together
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Open office floor plan
Dedicated Diversity/Inclusion Staff
Unconscious bias training
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Wellness Programs
Retirement & Stock Options Benefits
401(K) Matching
Vacation & Time Off Benefits
Generous PTO
Paid Holidays
Paid Sick Days
Perks & Discounts
Beer on Tap
Casual Dress
Commuter Benefits
Free Bus Pass
Stocked Kitchen
Some Meals Provided
Happy Hours
Fitness Subsidies
Professional Development Benefits
Job Training & Conferences
Cross functional training encouraged
Promote from within

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