Sawyer Stories: Sitting Down with Director of Sales, Arianna Maglio
Working at a start-up is one of the most exciting, fulfilling, and difficult journeys you can embark on during your professional career. You’ll immerse yourself around big ideas, brilliant people, and face unique challenges along the way.
When you’re on the sales team, it’s an even different ball game. You’ll get the opportunity to drive the business to new heights, while working with some of the most energetic and smart minds around.
At Sawyer, we’re building technology to connect parents with providers of the best enriching childhood experience, and our sales team is run by Arianna Maglio. She’s a leader, mentor, and has grown the team to new heights — all while still feeling like the underdog for most of her career.
We sat down with Arianna to chat about her experience, her hustle, and why you need a beginner's mindset to succeed. If you’re aspiring to join a sales team, you won’t regret learning about her journey.
Thanks for taking the time to chat, Arianna! Tell me about your career? How did you start?
Before graduating from Fairfield University in 2014, I went to a career fair on campus and was introduced to a recruiting company called Insight Global. Luckily, I was able to nail down the job before the end of my senior year and started working there shortly after I graduated. After about 6 months, I decided recruiting wasn’t for me and came across a company (ironically from another recruiting company) called SinglePlatform, which is where I learned the foundation of how to sell SaaS software to small businesses.
Do you think there are similarities between recruiting and sales?
Recruiting is basically sales, you are selling a candidate to a company and vice versa. It is a lot about building relationships and finding new opportunities.
Was sales something that you always wanted to do? What was your first sales job?
I majored in Communications and minored in Psychology, so I really had no idea what I wanted to do after graduation. I actually started taking GRE prep classes the summer before my senior year thinking that I might want to get my Masters in something related to psychology/social work. Luckily, I was able to land a job with Insight Global, which is an IT staffing company that works with Fortune 500 companies and connects product managers with candidates in the tech industry.
How did majoring in communications and psychology help shape your career and what you wanted to do?
Important to learn the behaviors of people — sales is all about selling a service and doing a service for others. In a world that is so digital, having successful human communication and understanding the behavior of why people buy.
It’s interesting that a liberal arts education helped you succeed in a role that’s typically considered quite distant from that discipline. So, what do you think makes a good salesperson?
I always felt like the underdog. For example, when I started at SinglePlatform, I was the last person in my training class to schedule a demo. I always felt like I had to work harder than everyone else around me in order to achieve my goals. That being said, a saying I live by is “hard work beats talent when talent fails to work hard.” As long as you are putting intentional effort into everything you do and every call you make, you will become 1% better every single day. If you are making 10 more calls than everyone on your team every day, that’s 50 more calls a week, and 200 more calls a month, which is essentially 1–2 more selling days in the month that you now have over the rest of the team. Be willing to put in intentional effort, get gritty, learn from others around you, make mistakes fast, ask questions, and always have a “beginners mindset.”
Do you have any quick tips for up-and-coming sales reps?
It takes a lot of work outside the 9–5. Also, use your commute to pump yourself up. I did, and it helped me make 200 cold calls a day.
How did you land your job at Sawyer?
I actually heard about Sawyer through Megan Riley, who was the Sr. training manager at SinglePlatform previously. We ran into each other and she was telling me about Sawyer and how she was looking to start scaling the sales team (back in 2017) and shortly after, I sent her my resume and became the 4th sales rep to join the team in Feb. 2018.
How have you grown to be the sales leader you are today?
I always felt that it was important to lead by example. When I think about leadership, I think about serving others and producing leaders on your own team. Another thing that has been instrumental in my growth has been mentorship. I’ve had many mentors who’ve taught me, challenged me, and guided me through the process.
Could you tell me about one of your mentors and why they have been so valuable to you?
Megan, who was never my direct manager. Being able to see how she leads and her professionalism was really inspiring. She gave me all of her knowledge and helped me learn how to report to leadership.
How have you grown to be the sales leader you are today?
She taught me how to give feedback to reps. Feedback sandwich — what they did well, what they need to improve upon, and end on a positive note.
What is it like to be a woman in sales?
It’s very empowering. It takes a strong leader — you don’t necessarily have to be extroverted but you do need to be your authentic self. You don’t need to be like a man, find your own way and your own path. You don’t need to be overly assertive, you need to be true to the type of manager you are.
How do you manage peers? What are your management tips?
Set boundaries between a friend relationship and a manager relationship. Show people that you have their back, by showing up and advocating for them. Also, make it clear you would never ask for something from your team if you did not do it yourself. Empowering people to give feedback in a structured way. Showing empathy and professionalism
How do you motivate the team? What are ways you incentivize and help the team grow?
Ultimately, you’ll find what’s best for your team. For me, I incentive my team with monthly bonuses. One month everyone won iPads, AirPods another — we just needed to hit our team goal. If you’re really performing you’ll win a free trip to the key market you’re selling to!
How has the Sawyer sales organization changed since you became the leader? Do you think sales have been impacted by your leadership?
In 2020 we hit or exceeded our goal 9/12 months of the year, which never happened prior to my leadership. In 2021 we are on the same pace.
How did the Covid-19 pandemic impact sales and your strategy?
We had to pivot online. It was a massive shift. Due to covid, we had to sell an entirely new product feature and way of teaching classes. Being remote was a challenge — not having music, being next to other sales reps. Being alone and getting rejected all day. It took a bit of time to adjust.
What are the type of providers and sales targets you are going after now?
We’re focusing on key markets now, with an emphasis on enterprise and franchise businesses. We’re also selling providers on value with new enhanced features
Let’s finish with the biggest question there is — why is Sawyer a great place to work?
The people are amazing. The product is so strong — I have never sold a product as good as Sawyer. The belief in the company and the belief in the mission. It’s so valuable for both educators and parents. We are not just selling software, we are selling a community. Also working for a female-founded company. Different vibe — transparency, community.
Ready to dive into a sales role at Sawyer? Explore a range of open roles here. You’ll get to work with Arianna, and find similar beliefs in our mission.
