When is the right time to move upmarket, and how will you do it well? It sounds great to be able to sell to more people and sell bigger deals, but are you ready? Thoropass CRO Bryan Caplin and Head of Demand Generation Jenna Keegan share when you should move upmarket and 5 tips for how to move upmarket successfully.

When Should You Move Upmarket?

First, you need to know if there’s an opportunity to move upmarket.

  • Do you have customers who are using your product successfully now?
  • What does that TAM look like?
  • What do you think you can achieve?

You want to ensure you have cross-functional alignment and that this isn’t another squirrel you’re chasing. You need support from every department and function within your organization, even to lift off a pilot to go upmarket.

Make sure your product is ready. You’ll be plugging it into more complicated environments, and more people will use it.

If you’ve moved upmarket before, you know this isn’t an overnight success kind of thing. It will take time, so ensure you have the funding and runway to do it. It could be a 6-month, 12-month, or multi-year venture, so you want the cash to invest in an upmarket strategy properly.

Look at your team. Do you have a core portion of your team equipped to sell upmarket? You don’t need a full team.

Look at your board. Has someone there sold into this new ICP, whether an industry vertical or a larger customer base? You want someone who can give you the advice you need to succeed going upmarket and someone who will advocate for you in the boardroom when you run into the inevitable set of challenges early on.

Once you’ve decided it’s time to go upmarket, here are 5 tips for success.

#1: Build a Demand Gen Strategy

The first thing you want to think about is building or rebuilding a demand strategy. If you’re selling to small companies, deals are moving fast, and you’re talking to one, maybe two people tops at the account. Maybe you’re more reactive and planning for the quarter. But if you’re going upmarket, things will look different.

You want to think a couple of quarters out to really build this strategy. These opportunities are going to take longer to create and longer to close.

How can you engage these new users across the funnel? How do you figure that out? One way is by talking to your customers and prospects. Ideally, you should have some customers at the upmarket deals if you go on this journey.

Figure out what they care about, how they use the product, and how they describe success when using it. It might look different from the smaller companies you’ve been selling to day after day.

Start to figure out messaging and where to put it. Where do these groups of people hang out? What events do they go to? Are they part of other associations?

Remember, the bigger the company, the more specialized everyone you’re talking to is. It’s less jack-of-all-trade hires, so the knowledge and questions they’ll ask will look a lot different. Adjust your content, figure out what you can repurpose and what you have to build from scratch.

You may start with a small team or a full company function. Either way, ensure the demand gen team sits down with sales and decides which accounts to go after. Ensure you’re aligned with the sales team on what you want to accomplish as you go upmarket and build these demand gen strategies.

#2: Focus Your Sales Team

Today, you probably have a sales team built to run after your core ICP. Many of these folks may not be a great fit for moving upmarket, but hopefully, some of them are. You’re going after a different buyer with longer sales cycles, and it will require more product expertise.

You’ll probably need to be multi-threaded, selling to multiple contacts within an organization. And you’ll need patience because your sellers may have one every three weeks, but that isn’t going to work upmarket. So, find sellers inside your sales org who can at least get you started.

You’ll also need to look at your sales process. Right now, you may have 3-4-stage sales processes that work for SMB customers. Going upmarket may be 6-7-8 stages, and your 3-week sales cycle becomes 3-6 months.

Everything you have now will probably look different upmarket, including pricing. Find those individuals inside the sales org, not just AEs but SDRs and the customer success side, to find those who can serve this upmarket profile.

Test out this new process with a tiger team, and start slow to go fast. But don’t forget to go fast once you’ve figured out what’s working. Once you do, invest and go hard after this market and grow the sales team to serve that upmarket customer.

#3: Re-establish Competitive Advantage

Look at your competitive advantage upmarket. You’ve built a product and sales methodology for this downmarket customer, and it will look different upmarket in terms of what your customers are looking for and what the competitive set is.

Your product will need to evolve, so get your product org involved early. Can the roadmap support what these upmarket customers are looking for? If you have them, talk to prospects and upmarket customers to get their feedback.

Get product and product marketing involved in those calls early on because you will need to evolve the product quickly to serve upmarket customers, which takes a while. Make sure you can make that investment from a product perspective.

Pricing is a big one. You have your pricing strategy for down-market customers, such as how you price the bundle, packaging, etc. Again, it’s going to look different upmarket. It’ll also likely be wrong.

You want to test pricing by going to the market and seeing if it works. Evolve it and test it again. Listen to those Gongs, get customer feedback, and evolve from there.

Finally, compliance is going to be critical. As you go upmarket, a customer will ask you, “Hey, do you have a SOC 2? Let me see that report.” Don’t let compliance stall deals. 

#4: Level Up Partnerships

Not a day goes by on LinkedIn where you don’t hear about partnerships being a big pipeline source, especially as outbound gets harder. Hopefully, you’ve built a partnership ecosystem for SMB customers, but it’s probably a completely different strategy for what you need to go upmarket for a couple of reasons.

  1. Buyers upmarket are more sophisticated, looking for more expertise from you and talking to a different set of peers to get information about you. 
  2. Upmarket buyers are more concerned about product integrations than pricing. 

You want to find a new set of partners that serve this customer with a very similar ICP, and that takes time. The partner serving SMB customers differs from someone serving Mid-Market and Enterprise.

Technical partnerships are often overlooked. You’ve built your product today, and maybe it integrates with Salesforce or Hubspot CRM for your downmarket customer. When you go upmarket, they’ll likely want you to integrate with some legacy technology, like MS Dynamics or AWS.

Technical integrations and partnerships are almost as important as commercial ones, and you want to make sure your product and engineering team can support that.

Finally, don’t forget about service partners. Your upmarket customers will require a different level of service. Try to find partners that can help you there because that’s expensive. You want partners that can take some of the upmarket needs off your team’s plate.

#5: Anticipate Changes In Customer Success

You’ve decided to go upmarket, created demand, built the product, and built the sales team. Now you have upmarket customers. Evaluate what kind of service they will need and anticipate those changes. 

If you’re selling to smaller organizations, that responsibility likely lands on one person for their account. You’ll want to think about specializing your CS org, having AEs who manage relationships, renewal, and revenue, and CS managers who can handle more day-to-day product and troubleshooting.

As you go into these larger organizations with more complex environments, more onboarding, more users, and more internal change management that you have to help them navigate, consider hiring onboarding specialists. These people get up every day wanting to make new clients succeed on your product.

You may also want to hire strategic account managers if you’re going after these big whales. Some organizations have one strategic account manager who only handles one big account, managing that relationship and land and expand.

Many different business units grow a single account, and you may be surprised by how early you need to bring someone with that skill set to your CS org.

Consider how much you can do self-service vs. white glove and what that looks like. Some users in more specialized roles have more technical acumen but may also need white glove support. Whereas smaller customers may need help just getting started with some of the things upmarket customers can handle on their own.

As you go upmarket, you may want to bring on a dedicated customer marketer to stand up programs like a Customer Advisory Board and customer advocacy programs so you continue to learn from these organizations, engage them, and keep them loyal to your brand after all the work you’ve done to get them on your platform.

Bonus Tip #6: Don’t Abandon Your Core

A corporate executive board did a study 20 years ago now talking about the top reasons companies stop growing. One of those is abandoning your core and moving away from what made you successful in the first place.

While going upmarket requires dedicated resources, investment, and focus, you don’t want to get distracted by the shiny new toy. You’ve built a brand and a successful strategy for the market you serve today, so don’t forget about it.

You’re not doing one in spite of or to replace the other. Abandon your core at your peril. 

Key Takeaways for Successful Upmarket Expansion

  • Get cross-functional buy-in early. Make sure everyone is on the same page.
  • Develop a demand strategy and be patient. Some things may take longer to work, but they’ll still work. So, figure out what the early indicators of success are and give things time to cook.
  • Talk to customers and prospects to fill product gaps. Find out their pain points and learn how they use your product. Some may surprise you, so keep those communication lines open.
  • Level up partnerships for both service support and integrations you need. Trusted partners already working with some of these big accounts you want to close can open doors for you.
  • Take care of your base. Don’t forget who is keeping the lights on. Going upmarket is an add-on, not a replacement, so take care of that core ICP.

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