How To Develop, Manage And Scale Your Sales Team

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How To Develop, Manage And Scale Your Sales Team

Background: Adam Ryan, Head of Sales

Could you start with a little bit of background — where’d you begin your career, how’d you get into sales, and how’d you ultimately land at The Hustle?

Adam: I studied to be a high school social studies teacher in my undergrad. After a few short months of teaching 9th-grade, I realized that adults were more my speed. I went back to school to study Corporate Education with the goal of becoming a corporate trainer.
While studying, I worked full-time for a national nonprofit that had a cause close to my heart. My goal was to help them discover new donation opportunities. Leveraging these skills, I made the jump into advertising sales by joining a Series E Goldman Sachs-backed media company where I spent a few years as an individual contributor. This is also when I started to read The Hustle.
My next move was to Under Armour’s new Connected Fitness division (MapMyFitness, MyFitnessPal, etc.) where I was a senior member of their small advertising team trying to monetize the company’s largest purchase. During my time there, Sam and I started to talk more about The Hustle and how it could scale with advertising (we had known each growing up in St. Louis).
In August of 2016, I started to moonlight for The Hustle and help out where I could. This is when I started to fall in love with the opportunity. After lots of convincing to my wife of 2 months, I made the jump full-time to The Hustle as the 5th employee. Today The Hustle sits at 25 full-time employees- with 5 starting the last 2 months.


Q: How does one reach people outside their circle for B2B products? I’ve made people refer me and that’s definitely been easier than cold emailing, but how do I scale this? Yeah, inbound marketing is one thing. And we’re doing that. Is that the only way?

A: Having a holistic demand generation is critical at scale. Inbound, outbound, nuturing, and all the other marketing buzzwords that enable sales team success. Also, because something is harder (read: cold emails), doesn’t mean it’s wrong. Our team consistently uses outbound efforts with cold emails to gather the attention of companies we admire and want to work with in the future.

Q: What tools are you guys using to help your sales team identify prospects and get their contact information?

A: MediaRadar, Clearbit, and LinkedIn

Q: How targeted/segmented can we get with the newsletter?

A: We don’t target/segment based on demographics. We don’t believe in doing this unless we have first-party data, which you never provided us when you signed up! We do create custom content for each ad and that relevant content has allowed us to work with niche industries at a successful rate.

Q: Do you also target baby boomers in your marketing campaigns?

A: The only paid marketing efforts we make are for our Daily email. We don’t filter by age. We love us some Baby Boomers.

Q: What was the first thing you did when you landed at The Hustle, and the first sale you made there?

A: I started at The Hustle moonlighting when I was working at a publicly-traded organization. So the first thing I had to do was create a process to be effective for The Hustle while not getting caught. Then Sam sat on a call of mine with a marketer at a large company that I had a relationship with to see if I was blowing smoke. My first sale was for $2K and called The Fruit Guys. Sam sold some ads before I started, I believe the first was Wealthfront.

Q: How much did you know how to charge for advertising vs the size of your list? Did any of your team have experience in ad sales before this? How do you determine who is a good fit for advertising, since it does seem to be strategic?

A: I have worked at a few publishers in the past and fairly familiar with pricing models. Besides myself, no one of the original 5 employees had any experience in media or advertising. In many ways, this was a benefit. The experience I did have allowed us to create a scalable revenue model and recognize the type of hires we needed to grow quickly. In terms of who is a good fit, I always believe that The Hustle was a B2B and B2C media company – which then it was ensuring we only work with brands we admire.

Q: How did you manage and evolve, the sales … “carrot” for your team? Was a % of each sale? A fixed number when they reached a target? And that structure, has changed? When? For what?

A: Our structure from the first day in terms of our revenue model and commission structure has never changed. We want to ensure to incentivize a rep to exceed 110% and make a plan that matches that.

Q: How the heck do you make money off of a damn fine newsletter?

A: I’ll let Zuckerberg answer this one.

Q: Hey Adam, great work. I’m curious to know what ranks hustles daily story picks?

A: Thank you. Our editorial chooses each story based on what they believe you all will appreciate the most!

Q: What is the usual, go-to model for email advertising or sponsorships? Charge by volume, demographics match, length of content?

A: In the end, pricing matches impact. Whether you charge by length, volume, demographic, etc. It all goes to impact (conversions or brand).

Q: What sales methods and technologies are you leveraging? What are the primary revenue streams?

A: I’m not much of a traditional “sales method” person, but I do love reading The Challenger Sale. In general, a curious and problem-solving personality will make the best sales reps (in my opinion). Our primary revenue streams are advertising and event sponsorships.

Q: How did you find brands to and the appropriate point of contact in said brands to close sales deals – is there a certain platform you use or is it via all cold calling?

A: We almost exclusvely use email as a method of communication, until further in the sales cycle. Most of our decision makers live in email (so does our product) so it makes the most sense. We use all sorts of tools such as MediaRadar, Clearbit, and others.

Q: 1. Chargebacks!! For the love of all that is holy. What are the best practices, best simple-ish universal protection methods that can be put in place without losing customers?

2. Ongoing ad spend, how do you prioritize? How to you track customers through sales cycles (do you re-target, etc) and what has worked/not worked in the past?

3. It was not clear if we could ask questions to help our own businesses or what so here you go.

A: 1. Understand the data of your clientele. From my experience, if there is a deal size under X then the risk of a chargeback is high. We either don’t allow those deals or make them pay a credit card upfront. Mostly, it drives our AOV higher because people want to be trusted.

2. We use Salesforce as our CRM. I’m a big fan and always have been. We have some super tight processes in place to ensure we are staying on top of our accounts. We also have an amazing Client Success team solely focusing on renewals.

3. If there is anything you think I can help you with for your business hit me up at adam@thehustle [dot co]

Q: How did you start and scale sales funnels for the business? What social media tools and techniques did you use? Was there a lot of cold calling or was this calculated A/B testing running ads to targeted FB audiences?

A: We have two customers we need to acquire at The Hustle. 1 – advertisers 2 – readers of the email

To acquire advertisers our sales team are the best non-creepy stalkers on the internet. They use various methods to find relatable to the contacts they want to get in touch with and manage that sales cycle through Salefsorce. We have never paid for demand generation for our sales team (shocking I know). It’s been solely put on the back of our sales team to create those leads.

Q: How did you identify and initially begin building relationships with advertisers when The Hustle was just a young, doe-eyed, fresh-faced newsletter?

A: It was super difficult. One of the defining moments for us was when we had our first big call with one of the top companies in the world and they asked us to do something that was against what we stood for as a brand. We told them no and walked away, but was honest on the reason why. They called back a few weeks later and since then we’ve had a great relationship. Honesty, curiosity, and empathy can get you very far in building relationships – no matter the size of the company.

Q: What metrics have you found most helpful as you’ve scaled your sales team, and what tools do you use to measure them? How have those changed as your team has grown?

A: I’m not an activity based sales leader. I trust that the people we have brought onboard are superstars and world-class at what they do. I don’t need to hound them on emails sent, calls, etc. What we do track and incentivize are cold meetings set, renewals, and pipeline created. We measure all this in Salesforce. As we’ve scaled, we’ve paid even more attention to these 3 as they are critical to the business.

Q: What program do you use for your email marketing to subscribers? We’re looking to build marketing campaigns for prospecting and communication with customers. By the way, we are in logistics and transportation. Not the media industry.

A: SendGrid is the platform our email is built on. It’s been a great platform, but does require custom engineering work.

Q: How do I better manage consistently, efficiently putting out content for my business?

A: Consistency and efficiency start with organization. Create a calendar for yourself. This can start with a week, then a month, a quarter, and who knows maybe a year. You need to be organized in your thought process before you can do anything consistently.

Q: Do you sell/share your email list with agencies or businesses? If so, are you able to segment the list if we wanted to target Canadian users only?

A: We do not sell/share our list with any businesses. That is a hard no for us. Our business is email so it makes zero sense for us to sell our main product away!

Q: I have a personal blog with 2000 subscribers. I do not place advertisement there yet, but recently I started receiving such proposals from advertisers. I’m interested how to write a decent native advertisement text to give maximum value to both – my subscribers and my advertisers.

A: Write something that you would enjoy first. Choose a brand that you love yourself and write about it in the email. Don’t disclose if it’s an ad or not and see how people react. If you start from the point of what YOU think is great, then you learn your audience loves it, now you have a path on how to make advertisers happy.

Q: What was your biggest struggle in getting your team to buy into your vision, and how have you overcome that to grow where you are today?

A: Before we decided to build out a team we created a strong business model and revenue plan that could scale. That plan for the last 2.5 years has essentially been perfect (thank God). When we brought on a new hire the first thing I did was show them that plan. It was important for them to not just love The Hustle, be a fan of the email, but to buy into our process. Transparency is critical when people feel like they are taking a risk with you. I ensure that any vision is worthless if the staff doesn’t trust the person spewing the vision. Build trust, be transparent, and have a solid plan. That’s how you get buy-in.

Q: My co-founder and I started a drone tech company and are about ready to bring on our first salesperson (as we can’t scale without them). What are some tips or best practices you’d take for hiring the first one? How should we compensate them?

A: Hire someone that when they talk about sales processes and ideas on how to scale – you don’t really know what it means. The reason why is they should be significantly better than you at this job. If you hire someone to just do menial tasks and replace your current efforts, your business might scale, but it won’t reach it’s highest potential.

Q: How do you determine what to charge advertisers? What do they value most?

A: There are multiple variables mostly hard costs of our team and engagement. Most advertisers care about the engagement of the email such as opens, clicks, conversions, etc.

Q: Do you have any experience with landing partnerships rather than sponsorships/ads? How do you approach those differently and how do you define a success?

A: In the last few months we’ve started to explore more partnership opportunities. These are very different than sponsors/ads. The goal of a partnership is that both parties have a win/win AND they both bring something to the table that no one else can. For example, if some music label came to us and said we’d like to promote you on XXX to this audience that matches your audience perfectly – but we want this band to play at one of your events. This is a perfect partnership. They have a unique reach and opportunity for us and we have a platform for them. It’s a win/win.

If someone says: hey we sell t-shirts that we know your audience will love so let’s partner. How about you promote our brand and in exchange, we will pay X% of the revenue. This is not a partnership. The risk is mostly on us for revenue we can do better elsewhere.

My goal on the first call is to say: these are the tent poles of our company and our goals, how do you want to help me get there? Then we are all on the same page.

Q: So, how did you do it?

A: Thoughtful hardwork, a lot of Bob Seger, and celebrations with Montucky.

Topics: Startup

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