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.



Boston Company Spotlight - CarGurus

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 Maddy Alves - Director, SEM Sales and Account Management at CarGurus.

Building the world’s most trusted & transparent automotive marketplace

Maddy Alves Director, SEM Sales and Account Management


What exactly does CarGurus do?  

CarGurus uses proprietary technology, search algorithms, and innovative data analytics to provide unbiased insights on car pricing dealer reputation and vehicle history, making it easy for shoppers to find great deals from top-rated dealers. CarGurus also helps dealers and private sellers quickly and easily market their vehicles and connect with ready-to-buy shoppers. Currently, we are the #1 automotive site per comScore when it comes to metrics like monthly visitors (according to the comScore Media Metrix Multi-Platform, March 2018, U.S.).


Why is it a great platform and product for dealerships?

CarGurus was built with the consumer in mind, which ultimately means that we are providing dealers with qualified, ready-to-buy shoppers. Dealerships work with CarGurus because we deliver an efficient customer acquisition channel driven by the volume of high-quality connections to our users. We not only offer products that help dealers acquire these customers and build their brands, we also help dealers market and sell their cars more efficiently.


What is SEM and why is it important to dealerships?  

SEM stands for Search Engine Marketing which is an advertising solution that utilizes search engines like Google and Bing to advertise their business. SEM is one of the largest automotive digital marketing investments and is extremely competitive, it is one of the most important tools for dealerships to drive direct traffic to their own website where they get the highest quality and converting shoppers. CarGurus leverages a robust automotive search data set, years of investment and industry-leading technology to provide unmatched results and scale for dealerships.


Why did you decide to become a sales professional?

I decided to become a sales professional because it gave me the control and autonomy to be as successful as I wanted to be. There is a lot of freedom in knowing that you have that type of direct control over your success. However, sales roles and cultures can differ from company to company, and I also wanted to work at a place that supports and fosters a creative, autonomous environment.


What does a top rep look like at CarGurus?

A top rep at CarGurus is adaptable, hardworking and determined. As I previously mentioned, we have an environment that respects rep autonomy and creativity - it’s all about the way you harness them both. A top rep will take complete ownership of their business, grind to get results and are also an awesome person to work with.


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

There are definitely those perks you can read about online such as free daily catered lunches, an abundance of snacks, transportation reimbursement, and a free gym membership. However, while those perks are important and are more than appreciated, they could technically be offered by other companies as well. The real excitement comes from the people a.k.a “The Gurus” and some of the amazing abilities and talent that reside here. I highly recommend that anyone interested in becoming a Guru should check out CarGurus on LinkedIn and read some of the shared-first accounts of why people like working here. They’ll see that we truly have a collaborative culture with positive, optimistic people. Reading these accounts represents that awesome feeling I have every day when I walk through the door.


Interested in joining the CarGurus team?

Visit Here


About the Author - Maddy Alves

Maddy has been with CarGurus for nearly four years, she started there as an account executive and has gone on to build and lead various sales teams during her tenure. Prior to CarGurus, Maddy worked at UTC and TechTarget in inside and outside sales roles.





Boston Company Spotlight - ezCater

Welcome to Boston Company Spotlight featuring Nicholas D'Ascensao - Vice President of Sales at ezCater. Our goal is to highlight local influencers, resources, and opportunities for our Top Rep Boston Community!  

ezCater is the only nationwide marketplace for business catering. ezCater’s online ordering, on-time ratings and reviews, and 5-star customer service connect business people to reliable catering for any meeting, anywhere in the United States.





ezCater connects business people with more than 60,000 caterers across the United States. Business people who need catering get an easy, reliable, and rewarding way to order it. Restaurant and catering operators get catering orders, operational support, and insights they can act on.

We’re not just a great website. We have a team of 5-star customer support professionals who are ready to help. Call us and a real catering Ninja will answer. No “Press 1” nonsense.



Solutions for Business People

Placing catering orders for work can be taxing and time-consuming, and it’s one of the many tasks our customers face. ezCater’s online marketplace streamlines the process so busy business people get more time back in their workday. Our customers say it best: we make their lives easier.

Solutions for Caterers

The restaurant and catering industry is tough: competitive, fast-paced, and stressful. ezCater’s off-prem solutions help restaurant and catering operators grow their revenue and customer base. Operators get a variety of efficiency-boosting tools so they can focus on what they do best: making delicious food.



Our sales team has two sides. Caterer Sales reaches out to caterers and restaurants. National sales onboard business people and businesses. Both groups — caterers and business people — have little time to spare, and both save time and effort with ezCater’s technology and customer service. We make these people’s lives better. Their words, not ours.



We’re the only nationwide marketplace for business catering (not just major cities), we have top-notch technology, and our customers love us.



ezCater is where amazing people come to work with other amazing people to do amazing things. I see other companies hire a bunch of salespeople, cut the ones who don’t succeed and keep the few who do.  We set the bar higher at hiring phase so when you get here you are surrounded by truly elite talent and teammates that will help bring out the best in you. We don’t have a preconceived notion of what makes an amazing rep and in an interview, it's not uncommon to not even be asked for your resume.  We hire people, not paper. Which is reflected in our team. We have Ivy League grads and then we have people who never went to college. Whatever their experience level or background, we see the greatness in people and we have a proven system to unlock it.

With the greatest talent in Boston and the greatest tools and systems in Boston, we have curated an incredible and low-pressure yet high-performance sales environment. Sure, I’m responsible for a bunch of performance metrics, but I don’t impose those metrics on my team. All that I ask for is attitude, effort, and respect (we are all equal). Since my team gives me those, the metrics take care of themselves. This opens up time for discovering better ways to do things, time for personal development and mentorship, and time to prepare for the rest of your career.



ezCater specializes in recruiting the ‘rising elite.’ We pride ourselves on the ability to find, recruit, develop, and mentor Boston’s next generation of elite sales talent.  We like to think of ourselves as the Harvard/MIT of sales education in Boston. We don’t hound our reps to make calls or send "x" amount of emails a day. The type of people we attract knows that doing the basics is part of the job.  What do we push our reps to do? We push them to think. We ask them to think about what is working and what could be made better. We push them to think more broadly about what we are not doing that could help move the business forward.  We want our amazing people to bring their entire brain to work and to use it to its fullest potential. Our top reps eagerly push limits, test things, and explore new ways of improving processes. They thrive in our incredible culture of flexibility and autonomy and go out of their way to take on more and help those around them.



There’s always something to look forward to: the next exciting challenge, free catered breakfast every Monday, free catered lunch every Wednesday, free Beer O’Clock every Friday, a kitchen (three, actually) always full of up-for-grabs snacks, cupcakes and other treats, softball games, an annual ski trip, unlimited vacation… We’re in an awesome location in Downtown Crossing, generous commuting benefits make it easy to get here, and a great benefits package keeps us healthy and happy.

 Interested in joining the team?

Visit Here


 About the Author - Nick D'Ascensao

Nick is an award-winning sales expert with over a decade of experience building high velocity inside sales teams at hyper-growth start-ups. He specializes in creating the recruiting systems, sales processes, and training programs that ground organizations for their next phase of growth. During his career, Nick has held sales leadership roles at companies including Yahoo!, Criteo, (IPO), Jumptap (Acquisition),  Millennial Media (Acquisition), and AOL.