Boston Sales Summit - Highlights!

With over 250 Top Rep Boston community members in attendance, sales leaders from Boston’s fastest growing tech companies, and NBA Champion Brian Scalabrine as our Keynote Speaker, it was fantastic Sales Summit!

In case you missed it, check out our highlight reel below!

We would like to thank all of our participants!

Keynote Speaker

NBA Champion - Brian Scalabrine

Keynote Speaker - Brian Scalabrine

Thank you to our event sponsors!


2019 Event Updates Coming Soon!



Boston Company Spotlight - Toast

As we look to highlight great local companies and sales opportunities for the Top Rep Boston Community, we wanted to welcome a new Boston Company Spotlight feature with Adam Mavrikos - VP of Sales at Toast.

Toast is the fastest-growing restaurant technology platform in the U.S.

Adam Mavrikos - Vice President of Sales

What exactly does Toast do?  

Toast simplifies restaurant operations by combining POS, front of house and guest facing technology on a single platform.  Everything we do is about helping the restaurateur run a more efficient, profitable business and we do that by focusing on the guest experience first. Our products are easy to use, thoughtfully designed, and built exclusively for restaurants.

What problem does it solve?

Toast helps restaurants be more efficient when they are busy, such as turning tables faster at peak times. In parallel, Toast helps to boost revenue when they’re less busy, with online ordering and loyalty programs for example. We care about our customers a lot, so it’s rewarding for all Toast employees when we hear stories about how Toast has changed their businesses and consequently, their lives.  We have a customer who grew revenue by 20% annually upon launching Toast hand-helds, this was after being flat in revenue for decades. Another says their servers are on pace to make an extra $7,000 per year in tips because of Toast. We sign up dozens of restaurants on Toast every day, and stories like this are why.

Why is it a great platform and product for local restaurants?

We made some very intentional decisions when building the product.. For example, being an Android based platform vs iOS gives our customers better pricing, more options for hardware, and greater flexibility in customizing the software.  For example, many of us have used a guest-facing kiosk at a large chain like Panera Bread and had a good experience. But Panera is large company with literally millions to invest in this. (They did!) Now with Toast, local restaurants can harness the incredible ROI on guest facing kiosks for about $100/month.

Why did you decide to become a sales professional?

I wanted a way to have a strong influence on my paycheck based on how hard I worked.  Actually, I would have liked to have started my own business by now as a way to do this, but honestly I found myself having too much fun working for cool scale ups like HubSpot and now Toast.  I also like solving problems, helping people, and learning new things. Sales is perfect for that. My old man told me a long time ago that if you can become really good at sales, it doesn’t really matter what the widget is.. good companies will always be looking to hire you. Turns out that’s very true.

What does a top rep look like at Toast?

Like at other companies I’m sure, the best Toast reps are hardworking, coachable, smart and motivated.  We find the best of the best are proactive about their business, humble, adaptable, have a life-long learner mentality and a unique passion for our mission at Toast.  It’s also a very diverse group in terms of previous experience. We have former restaurant managers, minor league baseball/hockey players, stock brokers, etc join as entry level players and earn their way to six-figure Account Executive positions within a year through our training and career progression program. It’s all about finding the right Toast DNA it turns out.

What are some perks or benefits that make Toast exciting to work for?

Can I rant here for a sec? Very passionate about this topic!

Toast’s buying persona, growth rate, and professional training program make Toast uniquely qualified as the best place in Boston to launch a sales career.  We of course have a great culture, beer fridge, unlimited PTO and other common perks you see at tech companies. But Toast is unique for people who want to be in sales in 6 ways:

1) The only way to get really good at sales is by having hundreds and thousands of sales conversations with prospects.  You can read all the books you want but experience counts in sales. And each call is an opportunity to get better as a sales person.   So my advice for people who want to get into sales is look for companies who

A) have a buyer persona who actually answer the phone,

B) have an insanely strong funnel of inbound leads, or

C) Both!

Now Toast sells to restaurants, our prospects HAVE to answer the phone! And our marketing team rocks, so we have the inbound machine cranking as well. At some companies, it could take years before you have your 1,000th sales call.  But at Toast, that 1,000th sale call probably happens in your first year,, so your skillset as a salesperson will have been accelerated significantly. Whether inbound or outbound, the ‘leads’ we call all answer the phone...some will even invite you in for a meal!

2) Once on the phone, our prospects actually listen! Especially when fellow restaurateurs in the area are using Toast successfully because restaurant tech is top of mind right now..  It’s a big deal if your neighbor is using Toast. The power of localization in our prospect base + the success of Toast customers nearby = fruitful prospecting and personal sales development.

3) Do you know how many different types of personalities and business models you encounter when selling to restaurants? It’s awesome, fun too and again, a fertile ground for new salespeople to get good, really fast.

4) Our sales training is world class. We are aspiring to build the best sales development program in Boston.

5) Our career progression is results based all the way. It’s clear, attainable, and rewards top performers.  We’ve had over a dozen SDRs get promoted in just the last 6 months into closing roles, nearly doubling their OTEs.

6) We have a field sales team! Want to live in Nashville, Austin, Miami, San Francisco, etc.? Great, come crush it with us in Boston for a year and write your own ticket. Want to stay in Boston? No problem, our inside team is booming. The upward mobility at Toast is nearly limitless right now. Come join us!

Interested in joining the team?

Visit Here

About the Author - Adam Mavrikos

Adam is currently serving as VP, Inside Sales at Toast.  Before that, Adam was an early member of the HubSpot sales team in 2008.  After helping HUBS grow to 1000 employees, 10,000 customers, and a unicorn IPO, Adam left to help apply those learnings and ultimately landed at Toast in 2015.  Over the last 3+ years, Adam has worked with and coached over 100 SDRs, account executives and sales managers at Toast. Toast recently raised $115 million in a Series D led by T. Rowe Price and Tiger Global Management at a $1.4 billion valuation.

Thank you for reading and sharing!



Catalina Wine Mixer 2018

What better way to spend a Wednesday night than networking on the Charles? Sales professionals from all over Boston gathered together last Wednesday to enjoy the gorgeous weather, live music, mingling, bites and a bit of sangria.

There was giant Jenga, cornhole, and frisbees. But best of all, there was a great mix of people from all different industries! We had people from CarGurus, ezCater, Breaktime Media, Logmein, Carbon Black, Drizly, and a number of others—gathered together to share ideas and make connections.

Towards the end of the event, the Top Rep Co-Founders Jarrett Mackin and Josh Ginsberg stood up to announce the upcoming Boston Sales Summit coming up Wednesday, October 10th. They mentioned there will be sales workshops and live training, open panel discussions, and Q&A sessions with local sales leaders from Cargurus, Drift, Drizly, Hubspot, and Smartsheet. Plus, a local Boston Sports Icon! More details coming soon.  

We want to give a special shout-out to Cargurus for hosting us, Lyle Brewer for the awesome guitar playing, Brandon Colby - for the great highlights, and everyone who came out to the event! We hope to see you all soon.

For those of you who don’t know Top Rep Boston. We’re an organization for sales professionals in the Boston area who are developing and growing their careers. Top Rep Boston offers practical resources and access to exclusive networks and content!



About The Author - Brianne Shelley

Brie's been an active member of the Boston startup community for the past six years and currently an Account Executive at EzCater. She's been on the ground floor helping companies rapidly grow, creating avenues for lead generation and always pushing for bigger ideas. Working in shared spaces, local coffee shops and diverse offices, she's written content for a number of different personas, successfully managed companies' social media profiles and closed deals as a top performer on the sales floor.



What is OTE?


When you start your search for a sales position, you’ll see things like OTE $90,000 or $55k base, $85k OTE.  But, what does this really mean?

In order to properly gauge sales opportunities, it’s important to understand the concept.

OTE, or on-target earnings, is a metric that provides the forecasted compensation for a particular position based on the expectation that you’ll hit certain performance targets.

In sales, this number is typically made up of your base salary plus your expected commissions.

Although companies often post this number with their job descriptions, take it with a grain of salt.

Some view OTE as a conservative estimate that the majority of employees are required to hit, while others view OTE as a stretch goal that only the top performers will achieve.

To get a better understanding of how much you’d make at a particular company, ask the hiring manager how the current sales team is performing based on the company’s stated OTE. What percent of them are at, below or above it?

Extra credit: Ask to see the commission report that sales submit to finance. If they don’t feel comfortable showing you, tell them to block out the names and only show you the representative average performance. This will give you the best idea of what to expect.

Since you’ll be starting with a clean slate, it’s also good to ask what the OTE including ramp typically is.

Oftentimes, the OTE number listed in a job description is based on a fully ramped rep. If you factor in the time it takes for a new employee to ramp up, there’s a good chance that number will go down.

Although ramp time is expected, make sure you know how long it will take so you can accurately calculate your expected earnings.


  • Understand OTE is a ballpark number representing your potential yearly earnings.

  • Before you accept a job offer, make sure you have an open discussion with the hiring manager about OTE and the probability of hitting it.

  • Keep in mind, the highest ratio you’ll typically see for base salary compared to variable pay is 50/50. Ex. 50k base 100k OTE. If you see one above that ex. 50k base 150 OTE, understand that most of that money isn’t guaranteed, be careful!


About The Author - Brianne Shelley

Brie's been an active member of the Boston startup community for the past six years and currently an Account Executive at EzCater. She's been on the ground floor helping companies rapidly grow, creating avenues for lead generation and always pushing for bigger ideas. Working in shared spaces, local coffee shops and diverse offices, she's written content for a number of different personas, successfully managed companies' social media profiles and closed deals as a top performer on the sales floor.