How to Build a Sales Operating System with Madison Carmody from Hubspot

Madison Carmody is a Sales Manager for Hubspot. Currently residing in Singapore, she looks after the company’s sales teams in Asia.

We were thrilled to have Madison onboard at SalesCollider’s Revenue Roadmap Workshop in Singapore last month. The event was hosted by 500 Startups with partner sponsor AWS at Singapore Management University and sponsored by Hubspot, Stripe and Dropbox. Over 40 founders from five ASEAN countries came to work with our team on building their B2B revenue strategies.

Madison’s expertise in building and growing sales operations was of great interest to our founders. They are all, after all, working like hell to find their footing in a market with no shortage of competition. In Madison’s words, “Starting is a company is easier than ever, but scaling is harder than ever.”

When Hubspot started in 2006, she points out, the company only had 5 or 6 competitors. If they started today, they’d be looking at a competitor pool of around 5,000 companies. Sure, the cost of starting a business is much lower, but gaining traction is much more difficult.

So what is a founder supposed to do? How can a company and its team stick out amongst all of the noise? Madison was kind enough to sit down for a quick chat to answer some of our questions and offer advice for startup founders trying to pick up momentum.

The Biggest Challenge for Startups

In Madison’s opinion, the biggest challenge for founders is allocating their time properly. After all, there are so many things that need to be done and only so many hours in the day.

“When it comes to growing and scaling, one of the biggest issues is that there are so many different hats you have to wear on a given day,” she says, “Sales, marketing, finance, customer service…it all needs to be done and of equal weight.”

Don’t just make sure that everything gets done. Do everything in a way that promotes growth. “If you’re doing it all, have you got an efficient system in process to ensure that you’re consistently building?” she asks, “Do you know what’s working and what isn’t?”

Mapping the Sales Process

Keeping a written record of your sales process will enable you to figure out how to sell consistently. “A growing business needs to be able to find a repeatable process,” she says.

She also points out that tracking the sales process will help founders to build a better sales team as the company grows. After all, you can’t just genetically clone your best salesperson.

“Even if you have a really good sales rep who can manage to sell anything to anyone,” she says, “you need to know what has worked before you bring on the next person. You need to know how to train them so that you can continue to build.”

Entering New Markets

Thinking about taking your startup international? Not so fast. Take a step back and think about where and why you’re expanding.

Madison suggests looking at your Total Addressable Market before you decide it’s time to expand. Your TAM is the group of people who not only would buy your product but who can also afford it and who you are capable of reaching.

Looking at your TAM, she says, “will help you to keep a critical pace in thinking about who you’re actually trying to target. Do you know who your competitors are and what your opportunity for leveraging a certain country is?”

Going International

If you do move forward with an expansion, it’s important to keep in mind that selling in new countries may be different than you’re used to. Having been a crucial part of Hubspot’s international expansion, Madison has firsthand experience in getting to know new markets.

“A lot of businesses that want to go global make the assumption that selling into one region is the same as selling into another,” she says, “As a U.S business entering the market in southeast Asia, we learned some hard lessons pretty quickly.”

One of the lessons they learned, she explains, is how to maintain a sales process that can adapt to new environments. This means rethinking your buyer persona and researching the needs of customers in a specific region.

“The goals and challenges of someone in the U.S are going to be very different for a business who is getting started in southeast Asia,” she says, suggesting that founders go out and meet their customers before making any assumptions about them.

Getting Over the Fear of Sales

At SalesCollider, we’re all too familiar with founders who are anxious about selling. Madison’s advice: stop thinking in terms of pitches.

“Have the confidence to have a conversation,” she says, “Rather than pitching and overcomplicating it, [remind yourself that] you’re speaking to another human. Just have a conversation.”

It may help to limit the formalities that can accompany a traditional pitch. “Do it in a non-formal setting,” she suggests, “Take them for coffee or whatever that might be.”

It’s also important, she points out, that you stay curious about your customer. Selling, after all, is about giving the customer what they need. “You need to be able to get them talking,” she says, “By listening more than you’re talking, then you can consult on a solution that can solve their problem.”

Once you do get around to talking about your own product, Madison says to “Leverage your credibility with cases studies. That will bring some of the guards down and make it easier for you to have a discussion.” She also advises that you research the company’s existing customers in order to understand the problems they’re working to solve. Having more knowledge about the prospect will make you more confident in your interactions with them.

Ultimately, knowledge is the key to success for startups. The more you understand about your potential customers, your individual prospects and your own sales process, the more likely you’ll be able to make space for yourself in a pretty saturated market.