The 5 Biggest Achievements and Lessons of The Hustle Sales Team in 2017

Insights into the wild ride of one of the fastest-growing media companies in the country.

January 9, 2018

Almost a year ago I wrote about launching an advertising sales team with $300/month. Then, I gave an update 6 months later about how to scale revenue 26X. Now it’s time for another update — a full year of building out The Hustle’s Advertising Sales team and growing the Events team.

Looking back at these posts makes me laugh, feel a sense of pride, and reflect on all that we’ve learned. I hope that some of you sales and media leaders can find this as useful as it is for me to document.

Note: I’m structuring this post a little different than the past ones. First, I’ll cover my 5 proudest accomplishments for The Hustle’s advertising/events teams in 2017 and then my personal 5 biggest lessons learned. After each one, I’ll include a little takeaway on how/why I thought this happened.

My 5 Proudest Achievements for The Hustle advertising and events team

Achievement #1: The Hustle hit their revenue goal every quarter in 2017

In the back half of the year, we focused on selling longer-term deals with our top partners. This allowed us to go into most months with the goal either complete or exceeding 90%. The impact of this was less “fire sales” and creating a firm minimum of our ad products.

The combination of higher average prices, longer-term deals, and increased demand allowed us to hit or exceed our team quota each quarter with relative ease.

Achievement #2: Renewals in Q4 were north of 68%

How? Relationships and performance, in that order.

Our client success team was completely elevated the back half of 2017. All new clients received handwritten thank you cards, The Hustle stickers, and more.

For our top clients, we created custom reports based on what THEY needed to show their boss/team. We built relationships by being honest when we screwed up and setting realistic expectations. On top of building relationships, our flagship product (the daily email newsletter) improved exponentially in terms of engagement.

We hired a strategist in Q3 to ensure we created the best ad copy for our audience, The Hustle brand, and our partners. What all media sales teams need to know is this: when media buyers sense your laggy response time, sour attitude, or apathy towards them they’ll soon be spending with someone else.

I don’t care how great your product performs. If you’re an a**hole, exaggerator, or pushy salesperson then you’ll never renew your clients.

Achievement #3: Total advertising bookings going into 2018 were 43X larger than what bookings were going into 2017

This is thanks to a combination of many things: our sellers building relationships, our client success team creating unique strategies for each partner, a new VIP program, the best editorial staff, and a lot of hard work.

I say all the time that anybody can sell, but predicting your sales is a real talent. Each individual seller and our Client Success team predicted targets for each client and their predictions were nearly perfect.

On top of an amazing team, we also had a little external motivation. Meet our sales team’s “fish board.” For $100, I printed the largest poster you could possibly print at Kinkos with a man fishing and then printed, cut out, and laminated 3 different size fish. Each fish had the logo of clients and the $ amount predicted to bring in before the end of the year. The former teacher in me was waiting for the day I could laminate again.

This board provided the extra motivation to have our sellers “catch the whales” to help us hit our goal.

Achievement #4: Our new event series, 2X, sold out in less than a week

Ah, the classic formula of engaged audience + great content + fantastic event planning.

If you haven’t heard of 2X, it’s an evening event that celebrates the stories of female entrepreneurs and business leaders. In other words, 8 badass women each get 10 minutes to tell their story. 2X is the brainchild of the first employee at The Hustle and now our Director of Events, who saw a huge need for a platform like this one and nurtured it to where it is today. The event was first launched in March. We launched it again in October and sold out The Palace of Fine Arts in SF in less than a week. 2X focuses on speakers who have great stories to tell, no matter their title or company.

To make this happen, we ensure the venue enhances the experience while focusing on creating something that we, The Hustle team, would enjoy. The same same formula worked for 2X in LA with similar results and now we’re bringing the event to the rest of the country in 2018. I can’t wait.

Achievement #5: The Sales team reached their own personal goals including buying an engagement ring (and getting engaged), living debt-free, traveling abroad, buying a house, and more.

Our team is taught to trust the process, to work as hard as they can, and always enjoy the benefits from that hard work.

The Hustle has had a generous PTO policy from the beginning and I encourage the advertising sales team takes full advantage. I’m not a big NASCAR guy but I think of advertising sales similar to a race when it comes to taking breaks.

Right before the fuel tank is empty you need to take a pit stop. If you don’t stop to refuel, you will lose the race. And when you take that stop as a driver, you have an entire team working to help you so you come back faster and better than before.

Out of all the goals, we accomplished in 2017, nothing makes me happier than our team achieving their personal goals and taking healthy breaks.

The 5 Biggest Lessons from 2017

Lesson #1: Hard conversations have to happen, embrace them

This goes for clients or employees.

Throughout the year I had to have many hard conversations including letting someone go from the team, telling a client we totally screwed up their URL on Black Friday, misunderstandings with others in leadership, and many more. These conversations are difficult and make everyone a little weezy in the stomach. They also define the relationship you have with the person on the other side.

At times I’ve had a hard time with this due to my attempt to always have a positive attitude. There were moments this year where I wanted to try and put a positive spin on a negative situation. While it might seem like a good idea, in reality it’s losing trust. If you screwed up, then admit it and have a solution. If you have to tell someone bad news, don’t sugar coat it. What I’ve learned is that being straightforward in difficult situations amplifies the positive moments even further.

All things in life come with positives and negatives so don’t expect management or building a team to be any different.

Lesson #2: Culture is a real thing and takes a ton of effort

This might be one of the biggest lessons and something that a paragraph can’t teach.
There were moments last year where I questioned the culture being created among our sales team — whether if it was wrong or if the good parts could sustain.

The answer is still unknown. What I have learned, however, is that at the heart of a great culture lies in sincere actions. Employees can tell when a company or manager creates something that doesn’t truly have their interests in mind. My trick is to show sincerity through consistency in my actions.

I do this by creating team incentives throughout the entire year, rather than the Friday before the end of the quarter when I want the team to put in a long day. Additionally, I make sure to tell them what I expect as soon as I can instead of waiting to set last-minute goals.

My thinking is that if you’re authentic and transparent in everything you do, you will create a culture that enables employees to care about each other. The more your employees care about the company and each other, the less you will have to worry about hitting your goals.

Lesson #3: Think big early or you will never get there

If you doubt you’ll grow to $100M or more, then you never will get there.

The mindset has to be there but so do your actions. I learned in 2017 that you have to implement the software that will scale with you, hire the people you want to go through the highest of highs and the lowest of lows with, and recognize the processes you created month 1 probably need to get changed in month 6.

Invoicing our clients is an example of needing to adapt our processes. Historically, the Client Success team sent invoices manually through It worked great for a while, then Q4 happened and the amount invoices needing to be sent increased drastically. This is when we decided we needed a new process and different software and are now in the middle of migrating to an automated way to send invoices via Quickbooks/Salesforce. This process will save our lean and mean team 10 hours a week which is huge.

If you’re wondering, my favorite software to use as of today are Salesforce, Zapier, DocuSign, Highfive, and the Office Suite.

Lesson #4: Have a ton of fun and always take a second to celebrate

You know that old cliche, “If a tree falls in the woods and no one is around, does it make a sound?” The same thing applies to hitting your goals.

If you set a goal for the team then you need to take time to celebrate it or recognize you didn’t hit it. That’s just follow up and should be required. My favorite moment of this lesson was at the end of 2017 when our team hit a massive stretch goal.

We hit the goal at 3:30 pm on 12/21 and, right when it happened, we popped some champagne, hit the gong, and we hopped on a team-wide video chat. We all celebrated for 5-10 minutes, had one big cheer, and then everyone went back to work for the next few hours.

It was a textbook moment that showed a priceless memory can be created while still maintaining productivity in the workplace.

Lesson #5: Never stop asking for help.

I say all the time that we are a team of underqualified overachievers.

Before The Hustle, I had never hired an entire Sales and Client Success team, built a Salesforce platform, had the responsibility of collecting payments from clients, or had the responsibility of building out the P&L of an events business. Basically, I didn’t know how to do a lot.

What I do know is how to learn from those who have done it before me and learn from my past experiences. I meet with as many people as possible for coffee, beer, or a simple conversation at our office. Some of these people won’t teach you a thing and you’ll recognize that you know more than you realize. Others will make you walk away wishing you could meet them again the next morning for coffee (I actually met with someone for back-to-back coffees two days in a row).

I’m not much of a book reader or even a listener of podcasts. My learning strategy includes: YouTube for any tactical skills, BusinessInsider, and AdAge to learn where the market is trending, listening and asking questions to my peers and mentors, and learning by throwing myself into the fire of first-hand experience. It may sound cliché, but if you stay humble and hungry you will go much further than those who are too proud to ask for help.

That’s it, those are my proudest moments and biggest lessons from 2017. I’m excited and anxious to see what 2018 will bring… stay tuned for another update in 6 months.

If you’re interested in partnering with The Hustle, have any tips on how I could improve as a leader, or have any questions about what I wrote above, feel free to reach out to me directly [email protected].

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