Payments company Swipely, the simple way for merchants to understand customers and grow sales, is doing big things: just last week, the company announced a successfully completed Series C round, totalling $20 million, taking its total funding tally to $40 million. This announcement came on the heels of another great milestone – the company’s payment processing rate had doubled to $2 billion annually. Leading the charge on these great accomplishments was Matthew Oley, the VP of Sales at Swipely.
We recently had the privilege of speaking with Matthew on how his previous position at Seamless prepared him for his current challenges, his sales leadership best practices and how Swipely – an InsightSquared customer! – works with sales metrics and data to drive scalable growth.
1) You spent the entirety of your sales career at Seamless, working your way from the ground up to a Sales Director position, before choosing to leave and join Swipely. What prompted you to undertake this new challenge?
When I joined Seamless, I was the 15th employee. The team was amazing and the product was powerful for both the restaurant and end user. I watched that company grow to over 200 employees by the time I left.
When I was connected with Swipely, I saw many similarities to Seamless circa 2003 when I joined. I was impressed by Swipely’s team and the venture capitalists backing the company. I was also excited about Swipely’s mission to help local merchants succeed. I saw an opportunity to help build another impactful company and jumped at it. I joined Swipely in 2011 as employee number 15th and have been part of growing the business to over 100 employees in just 3 short years.
2) A big part of what you focused on at Seamless was on expansion – both national and international. What are the primary concerns and considerations when a company undergoes such an expansion phase?
The way I approach expansion, both when choosing markets and leads, is to focus on the right set of customers. I look for the cross-section of customers that will value our product/service and meet our financial model. With that understanding, my team uses data to prioritize markets and leads. As an example, at Swipely, we know that businesses doing half a million dollars or more in annual sales typically leverage technology to run their businesses, value our tools and are a good fit for our model. We look at a variety of data points, including annual sales, broadband access, Facebook activity and more to find those businesses.
It’s also important to hire the right type of salesperson when expanding. Someone who is successful growing an existing market with reference customers might struggle when breaking ground in a new market with little brand recognition. This is particularly true when expanding internationally. One strategy when hiring an expansion salesperson is to hire someone who has existing relationships with your target customers.
3) Many of your past direct reports have raved about your sales leadership (on LinkedIn, etc). In your opinion, what is the key to effective sales leadership?
First and foremost, I view myself as a coach. I think it’s important for any manager to hire talented people and position yourself as you working for them, as opposed to them working for you. I ask my team to think of me as a resource that can help them be more successful achieving their personal goals and our company goals. I’m no different than our CRM or training system – I’m there to help them win.
Second, I use data to make decisions and develop a success formula for sales reps to follow. I document that formula along with a sales playbook that outlines how to win at every stage. It’s all there – no mysteries or guesswork. You can’t expect your people to achieve their goals if they don’t know how to get there. Its like asking someone to drive to your house but not giving them directions. When goal setting with employees, I have found it to be effective to start at the end and work backwards. If someone tells me they want to make $X or sign a certain number of customers this year, we can determine exactly how many calls, demos and proposals they need to do in order to get there. We can then work together to put a plan in place to achieve that goal and hold each other accountable.
4) How important is sales and marketing alignment at Swipely? How do you focus on improving this alignment?
We view sales and marketing as two sides of the same coin. Sales will be more successful with strong marketing, and marketing will be more successful when the team has a good relationship with and feedback loop from sales. If you share the same end goal of delivering value to your customers, than everyone wins.
5) Swipely was named one of the “Best Places to Work in Rhode Island.” How important is this recognition to you and what have you personally done to achieve this?
It’s huge. Our people are our most valuable asset. They’re smart people who challenge each other and collaborate on exciting problems. We’re proud to be named one of the “Best Places to Work in Rhode Island” by Providence Business News, “One of America’s Most Promising Companies” by Forbes, and by Inc. as “One of America’s Top Job Creators”. The awards showcase that the team is building a great place to work. They also help us continue to attract top talent – shameless plug, we’re hiring!
As far as specific things we do, we put an emphasis on supporting employee career growth. We encourage people to take risks and believe in an open and honest culture. In fact, we have no offices and instead all sit together. We have a ping-pong table, and plenty of opportunities to get to know each other over free catered lunch or happy hours.
6) “Efficiency” is increasingly becoming a priority for companies, especially start-ups, working with more limited resources. How have you improved efficiency from your direct reports since you got to Swipely?
We leverage a lot of technology. We also focus on specialization. For example, we have a team that exclusively focuses on setting appointments, a team that focuses on closing business and a separate team that manages accounts once they become a customer. In order to provide a top notch experience at every level you need to have experts focused on those specific areas.
We also have adopted a culture that is focused on constant improvement. Too many companies adopt the mindset that if its not broke I don’t want to fix it. We understand that at a fast growing company what worked yesterday might not work tomorrow. We’re always looking for how to get in front of problems and do things better.
7) Before coming to Swipely, and then before using InsightSquared at Swipely, how big a role did data and sales analytics play in your day-to-day? How big a role does it play now?
I’m a data-driven person by nature. I use data in my professional and personal life to make decisions. Before Insightsquared, I ran into issues where I couldn’t get access to some of the data that I needed to inform my decisions. With InsightSquared, there are a number of data points that I can access which I spent a lot of time trying to pull and, quite frankly never could. Once I had access to that data, it helped me spot opportunities for improvement. Being at a startup that is growing and changing so fast, it is important to be able to look out ahead and InsightSquared helps me do that.
Swipely’s product helps merchants better understand their customers and grow sales using data. InsightSquared does the exact same thing for me that we do for our customers – give them the data to make smart decisions that grow sales and save precious time.
8) Where do you see the future of sales and marketing trending over the next 5 years?
Sales and marketing are becoming more of a science everyday. I measure everything and have a formula for success at each level of the pipeline. Since I don’t have to guess at what’s happening, I can spend more time tweaking and improving our processes.
More about Matthew Oley
Matthew is the VP of Sales at Swipely, a payments company that provides the simple way for merchants to understand customers and grow sales. Prior to joining Swipely, Matthew served in various sales positions – from sales rep to Director of Sales – at Seamless. He holds an MBA from New York University.
