1

The SaaS Playbook for Moving Up-Market

moving upmarket saas sales - featured image

SaaS companies tend to follow a typical path, and it almost always leads to moving up-market and enterprise sales.

In the early days, most SaaS companies sell to other startups for a number of reasons. Startups are more willing to be early adopters of a new product. Startups are less demanding than a big company both from a services and product perspective. Small companies require less customization. There’s also minimal feature requirements outside of the core product offering – SSO, SCIM, SOC2, Admin Permissioning, etc.

It’s simply easier to create a SaaS product for smaller companies.That’s why most SaaS companies focus on selling to other startups in the early stages of the company lifecycle.

But as SaaS startups mature, they usually start moving up-market. Someone (usually a VC) will point out that hitting your aggressive growth numbers will be easier if you sell to larger companies. You’ll need to acquire less customers to generate the same amount of revenue and bigger companies have a lower churn rate. This is why most SaaS companies eventually move up-market and start focusing on bigger deals.

This is what happened at Lattice.

Related: What is Complex Sales? An Explainer on Enterprise Sales

The Lattice Story

I joined Lattice as the 3rd employee, first revenue team member and the VP of Marketing. At the time, we had zero revenue. We started by selling to other startups, mainly YC companies. After a couple of years, we had built a solid SMB business, but realized that in order to hit our growth goals we needed to move up-market. This became the primary focus of Lattice over the last couple of years.

We hired an incredible sales team – led by Dini Mehta – to help pursue this mission and it became a company focus. We changed our product, evolved our marketing programs, and transitioned the sales team. This was all in an effort to increase our average contract value (ACV).

After years of hard work, we were able to significantly increase our ACV (5x+). We started to close some serious enterprise deals with the major players in the technology industry including Slack, Pinterest, Flexport and more.

During this journey, we learned a ton about how to move up-market. Those learnings actually inspired me to quit Lattice and start a new company – Dock – that helps sales teams manage enterprise sales cycles.

In the following article, I share what I learned from the march up-market, so you can do the same with your SaaS startup. Here’s what I’ll cover:

Foundations for moving up-market

SaaS companies need to have the right foundation to move up-market. It’s not an overnight process and requires a number of moving components across the company. When you move up-market, you’re changing the DNA of your business.

Mindset

The march up-market takes a company wide commitment. The CEO and executive team need to make selling to bigger companies a key part of the company strategy. The CEO needs to make the move up-market part of the company OKRS. They need to talk about it all hands. And have it be a constant discussion point when evaluating decisions across the company.

This commitment is important because the move up-market will literally take years to pull off. I’m not kidding. It will take two to five years to move up-market. Enterprise buyers typically have a certain window of opportunity every year to buy a new piece of software. If you miss this window, you’ll have to wait another year.

At Lattice, most of our enterprise deals originated years before. We met someone at a trade show, sent them an outbound email, or demoed the product. The company didn’t become a customer right away, but we started to build a relationship that we could nurture for the years to come. Eventually, this paid off and we were able to close more enterprise deals.

Define your ideal customer profile

SaaS companies need to define what moving up-market means by outlining key firmographic characteristics.

  • Number of employees / licenses
  • Product usage
  • Revenue number
  • Industry
  • Geography

Companies need to carefully consider their ideal customer profile. The ICP determines decisions across the company from the go-to-market to product strategy.

I typically recommend that companies start with a Core ICP. A customer persona that definitely understands the value of the product offering. This is your bread and butter customer.

Companies should also consider an Experimental ICP. A customer persona they aspire to serve one day. For this group, the company is learning what it takes to make this customer experience successful. They might not close revenue in this segment today, but it’s an investment for the future development of the company.

Team Effort

Moving up-market is not just on the sales team. It’s a team effort that touches everyone at the company.

Sales needs to work with the product team to figure out the right features to build for enterprise customers. There’s a number of enterprise features that every SaaS company needs to build, but each product will have a unique set of requirements.

Sales needs to collaborate with the marketing team to figure out how to attract enterprise customers. This starts with aligning around the ICP. From there, the marketing team can build a brand that resonates with bigger companies, and run account based marketing programs.

Sales needs to partner with the customer success team to make sure that the post-sales experience surpasses the customer’s expectations. Enterprise customers require a certain level of care and whiteglove service implementation.

At Lattice, we built an enterprise taskforce to foster cross team collaboration. The taskforce brought together different functional leaders from each department. Every week the team would meet to discuss initiatives in the company’s move up-market.

Pricing and Packaging

Companies need to structure their pricing and packages in a way that appeals to enterprise buyers and drives up ACV. Most companies will create a special enterprise package. These packages give SaaS companies flexibility when it comes to working with larger companies.

When putting together pricing and packages, there’s a few common pieces of technology that get put into enterprise packages. Examples include:

  • SSO and SCIM
  • Customized Training
  • Dedicated Customer Account Manager
  • Admin and Role Permissions
  • Deeper Integrations

These enterprise features are usually the incentive for the company to purchase the bigger package.

Companies also need to keep in mind that most enterprise buyers have less price sensitivity than SMB buyers. If they’ve decided that you’re the right solution, they will pay what it takes to solve the problem. But at the same time, procurement teams need to feel like they are getting a win. It’s an interesting dynamic. SaaS providers need to leave room in enterprise packages for volume discounts, while also making sure to maximize the account’s value.

Segment the sales team

As you move up-market in SaaS, Sales leaders need to break the sales team into different segments.

Selling to startups is very different from enterprise companies. SMB sales tend to be transactional sales – every buyer is pretty much the same and quick sales cycles. But for enterprise buyers, there’s a level of sophistication needed. Enterprise sales reps need to have business expertise, process management skills, and strategic planning to be able to close the deal. It’s a more strategic, creative sale.

The sales leadership team needs to match the skills of the sales team with the buyer. And that’s where segmentation comes into play.

At Lattice, we constantly optimized our different segments to match sales skills with buyers. We eventually created three different segments based on company size – SMB, Mid-Market and Enterprise. This structure allowed Lattice to pair the right account executive with the correct segment. AEs could then focus on getting really good at convincing a single ICP to buy Lattice.

I generally recommend that a company hires (or promotes) an exploratory enterprise sales rep to start to test the waters in bigger deals. This sales rep might not close deals right away. But they talk to enterprise buyers to understand product requirements and learn how to craft the sales pitch to appeal to the enterprise.

How to Attract Enterprise Buyers

Lead generation for the enterprise has changed dramatically over the last ten years.

In the past, enterprise buying was always a top down sale. You needed to start with the business and IT leader. Now with product-led growth, the buying decisions are more decentralized. End users will start to use software and then the product will spread virally within an organization. This motion is called bottom ups sales or product-led sales.

The end user engagement helps the sales team get their foot in the door. But every enterprise contract eventually requires buy-in from leadership.

Here’s a few ways I’ve learned that SaaS companies can start to attract bigger companies.

Define Your Target List

Marketing and sales need to work together to target the same group of companies. This starts with the target ICP that the leadership team defined. Based on this customer profile, marketing, sales and revenue operations build a list of companies and contacts.

Start with the company ICP, and then look at the contacts (titles) within the company. In enterprise deals, AEs need to work with multiple people at the target company. When building the list, the team should identify multiple people at the same company. This helps to build a groundswell of interest and support for your product.

To build this list, there’s a number of data vendors like ZoomInfo and Clearbit. These vendors help companies organize a list of target companies and associated contact information. LinkedIn is also always a helpful resource to identify target accounts.

Run Account Based Marketing Programs

Now that you have your target list, it’s time to run account based marketing programs (ABM). ABM is a fancy way of saying that you’ll focus your resources and attention on a specific number of accounts. The best companies on your target list.

The actual campaigns and programs may change depending on who you’re targeting. At Lattice, we did everything from sending direct mail to inviting target accounts to exclusive dinners to making custom content for specific accounts.

I’ve found the best campaigns are multi-channel. The best ABM programs combine the following tactics:

  • Personalized Emails
  • Hyper-Targeted Social & Display Ads
  • Retargeting Ads
  • Direct Mail
  • IRL and Digital Events
  • Custom Content
  • Personalized Landing Pages
  • Exclusive Communities

The target accounts are overwhelmed with the amount of marketing coming at them. They are forced to recognize your company as an important brand in the market and need to learn more about your offering.

Each touchpoint should feel hyper-personalized and exclusive to the buyer. Companies need to make buyers feel special and show how much you want them to become a customer.

Personalized Outbound Sales

Enterprise accounts need a human touch and that’s where outbound sales comes in.

AEs and the SDR team should work to build a relationship with different folks at the target accounts. The days of spray and pray outbound sales are over. Instead, salespeople need to take the time to write hyper-personalized emails. They need to catch a buyer’s attention and show how your product will solve a problem the company is facing.

Outbound sales needs to piggyback on marketing campaigns. The best sales targets are folks who have already interacted with a marketing campaign (or product) in some way. By using lead scoring, sales teams can prospect from a database of warmed up prospects. This will always perform better than only interacting with people who have never heard of the company before.

Marketing campaigns give outbound sales a reason to reach out. Instead of just bothering someone about buying your product, salespeople can provide value before they are ready to buy. For example, AEs can invite buyers to an exclusive dinner with the CEO or send them a new piece of research.

Sales and marketing need to work together to get outbound to work. It’s a team effort.

Invest in a brand that appeals to the enterprise

If companies want to move up-market, they need to look and act like a big company. They need to work on building a brand.

Building a brand can require advertising spend, but there’s also in-house solutions for companies to move the needle.

This starts with your marketing website. Companies need to have all the bells and whistles of a big company website. This starts with a premium design. But it also means creating different pages that are on big company websites.

Just go look at some websites like Workday, SAP, Salesforce. This will help you get a sense of all the things a mature business presents to their buyer. Now I’m not saying you go build all this right away, but you need to have the basics and keep building over time. Your website needs to feel robust and not like a new startup’s website.

At the very least, companies should create a dedicated enterprise solution page – here’s an example from Slack. These pages signal to inbound visitors that you have a dedicated offering for big companies. You’ll notice that the features highlighted on Slack’s page are barely focused on the core product. The page highlights other features like security and global admin support.

Beyond the website, companies should invest into brand advertising to make sure their brand is known. Enterprise buyers don’t want to buy from some unknown quantity. They want to make sure you’re a reliable provider.

Companies can create this perception by investing into big brand moments. This could be putting a billboard on the 101, investing in a big space at a tradeshow, hiring famous event speakers or running a Super Bowl commercial.

Obviously, you’ll want to build up to this over time. The main limiting factor will be budget. But the more you can have your brand in the face of bigger buyers the work you’ll become a known quantity.

When brand marketing is successful, it will improve all the rates in the funnel. Outbound sales will get easier, more demos will come in, and you’ll start to have higher close rates.

Get case studies from bigger companies

In order to close bigger deals, companies need to show successful case studies for enterprise companies.

When potential buyers come to your website, they want to see logos of bigger companies. As the sales cycle progresses, sales reps need to share case studies and ROI studies to show how you work for these bigger companies.

It’s hard to do this overnight. There’s a chicken and egg problem. If you start by selling to SMBs, then you won’t be able to have case studies from bigger companies.

You solve this problem through incremental progress.

Over time, focus resources on highlighting the stories from the biggest logos in your customer base. As you start to acquire larger customers, you’ll start to get bigger and bigger case studies.

Eventually, you’ll get that golden case study that proves you can work with bigger companies.

Get your foot in the door with product-led growth

One of the best ways to break into the Enterprise is through the end users. This product-led growth model means you get a bunch of end users starting to use your product. From there, they advocate for a bigger implementation across the company. This is the model used by companies like Slack and Dropbox.

Attracting an end user is much easier than acquiring the entire company as a customer. You just need to convince one person to try your product. It’s an acquisition motion similar to consumer or SMB marketing. Companies can rely on inbound digital marketing tactics – SEO, Organic Social, paid ads – to catch someone’s attention and get them to sign up.

That being said, PLG obviously starts with the product experience. The product team needs to create a way for end users to sign up for the product and get value. They also need to thoughtfully gate different features in order to set up a bigger deal across the company. The connection between pricing and packages and the PLG motion is essential to getting this all to work.

Managing the Enterprise Sales Cycle

You’ve gotten some interest from enterprise leads. Now it’s time to turn those leads into an opportunity and close the deal. Let’s discuss what it takes to manage an enterprise deal.

What makes an enterprise deal different?

Enterprise sales are very different from SMB deals. Here’s the key characteristics that make them different:

1. Many stakeholders

When selling to an enterprise, you need to sell across an organization, not just a single point of contact. You’ll need to find a champion. From there, you need to convince multiple levels of management, adjacent teams and managers. Once you’re past that phase, you’ll need to deal with legal, security and procurement teams. Across all these stakeholders, there’s competing motivations and incentives that you need to manage.

2. Champion empowerment

AEs need an internal advocate who can guide them through the company’s buying process. This champion gives AEs insider knowledge and collaborates with them to figure out the best way to sell into the company. As a sales rep, a huge part of the job is supporting the champion with whatever thy need to advocate for the product to internal stakeholders.

3. Long sales cycles

Selling to the enterprise literally takes years. AEs need to figure out how to nurture accounts and build a relationship. They need to provide value before the company is ready to buy. Along the way, AEs need to figure out the right moment to strike – when it makes sense to start a serious conversation around an evaluation. The AEs job is to be there when the buyer is ready to evaluate new software.

4. Complex customization

Enterprise companies require deeper customization for the product. They have a defined process that works for their business and they have a bunch of specific quirks that you’ll need to solve.

5. Dealing with procurement

Enterprise companies usually have a department dedicated to buying software. They have a very defined process that dictates the steps to make a purchase from legal to security to pricing. Enterprise sales reps need to figure out how to deal with purchasing teams and sure they bake in a pricing win for this department.

Related: 8 Surefire Ways to Shorten the Enterprise Sales Cycle

Five essential sales skills for bigger deals

There’s a number of sales skills needed for enterprise sales, but the most important five are:

1. Deeper qualification

Long sales cycles and complex customization means qualification is more important. This helps AEs ensure that the time they are spending on the long sales cycle will pay off because the company is a good fit. There’s a number of sales methodologies like Sandler and Meddic that provide a helpful framing for how to strategically approach qualification.

2. Personalization

Sales reps can spend more time building a personalized experience for prospects. Sales reps will often build a custom sales presentation or sales deal room to show how much you understand the buyer’s needs.

3. Patience vs. Urgency

Enterprise sales reps need to have the capacity to patiently work a deal over a number of years. They need to continually provide value and strike a balance between providing useful information and not being annoying to the buyer. But they also need to know when to drive urgency and strike while the iron is hot to push a deal forward.

4. Collaboration and Curation

Enterprise sales reps should think of themselves like a guide. They work with the buyer to help them reach their objectives and curate information to help buyers make a decision. Buyers and sellers should be on the same team. The goal is to do what’s best for the business, not just close the deal for the sake of it.

5. Project Management

Enterprise sales deals have a lot of moving parts. The modern enterprise sales reps need to push projects forward and align the team towards making a buying decision. One popular tool to drive alignment are mutual action plans, which provide a shared roadmap for getting the deal done.

Product-Led Sales and Proof of Concepts

Before making a big decision, enterprise buyers want to try the product before they commit over the long term. Depending on your product this can look like a classic product led growth motion or look more like a proof of concept.

Product-Led Sales Motion

The leading way this happens today is through a bottoms up adoption cycle, product led-growth. End users will sign up for the product and try it for themselves. As they have a positive experience, they’ll invite other folks within the company. Eventually, a large number of people at the company have been using the product.

When this happens, it’s time for the sales team to step into the picture. Every product led growth company eventually needs sales.

The sales process starts when a lead becomes product qualified (PQL). This is usually determined by a signal within the app. For example, a company has invited a certain number of users.

When the sales team steps in, it’s time for them to drive further product adoption. They act more like a customer success manager who recommends better ways that the team can take advantage of the product.

From there, the AE needs to identify the central decision makers for the purchasing decision. And figure out a product champion who can help advocate for the product to internal stakeholders.

Then it’s on the AE to start building a case for why the company should upgrade to the enterprise package. They want to create a package that makes it easy for the leadership team to understand the value of the product and why they need to offer. This package should be easily passed around, so that your product advocate can easily share with senior management as they build the case.

Here’s an example of what this buyer enablement package could look like for your company. You’ll notice this workspace has the following elements:

  • Product Adoption Facts
  • Benefits around the current plan
  • Security features (IT loves security features)
  • Pricing and packaging
  • Outline of shared next steps

Each of these elements has a purpose. The AE is both showing how deeply embedded the company already is in the product. And showing how much value the company is getting from the current offering. Then they make the case for WHY they need to upgrade. This usually comes down to unlocking a feature set, typically around admin, security or dashboards. From there, they show an easy roadmap to making a purchasing decision.

Proof of Concept Motion

For a more traditional tops-down-enterprise or a technical or expensive product, there’s often a Sales Proof of Concept (POC).

This is where the AE and buying team align on a trial period where the company can try out the product. Alignment up-front is incredibly important. Both sides need to align around the following elements:

  • Use cases
  • Current Challenges
  • Success Metrics for POC
  • Long term Objectives
  • Stakeholders
  • Timeline

A collaborative workspace like Dock, Google Docs, or Notion is a great way to drive alignment with potential buyers. Importantly, you need to agree on an upfront contract around success before you start the proof of concept. Here’s a POC template to align buying teams.

Aligning the Buying Team

As mentioned earlier, one of the biggest changes with an enterprise sales cycle is that there’s many more stakeholders involved.

Mapping out the stakeholders

Every deal will have a champion, but there’s usually other roles involved. Typically, you’ll see the following stakeholders:

  • Business decision marker (the boss)
  • Financial decision maker (the money person)
  • Cross-functional leads
  • End users
  • Procurement
  • Legal
  • Security

Enterprise AEs should use tools like LinkedIn or ZoomInfo to understand all the players involved on the buying team. From there, AEs work with the Champion to identify the best time to bring stakeholders into the buying process.

AEs should multi-thread accounts and build relationships across the organization. They should think about ways to get the two CEOs to meet or the CROs to have lunch. The more relationships will build trust and make it easier for the company to sign off on a purchasing decision.

Mutual action plans provide a shared roadmap for a decision

Managing the process across all these different stakeholders can be very involved. That’s why enterprise AEs will often turn to mutual action plans to provide a roadmap for the process. These action plans will detail the different phases of the process. You’ll typically see something like this:

Evaluation

  • Intro Call
  • Point of Contact Demo
  • Stakeholder Demo

Proof of Concept / Free Trial Pilot

  • Kickoff
  • Check-ins
  • Feedback Session

Formalize Partnership

  • Budget
  • Scope
  • Legal
  • Security
  • Signature

Implementation

  • Kickoff
  • Trainings

For each of these steps, there’s an owner, resources and a defined timeline. Many companies use spreadsheets to manage this process, but we also created a Dock template for companies to use.

Streamline information sharing and close deals with sales deal rooms

One of the hardest parts of the enterprise sales cycle is keeping track of all the information that gets shared back and forth. It’s hard for both the sales team and even harder for the buyers. Information is spread across email, slack message, the website and hidden attachments.

The leading sales organizations solve this challenge through the concept of a sales deal room. It’s a single destination for buyers to get the information they need.

Here’s an example of a sales deal room.

sales deal room example - gif

As you can see, this deal room includes all of the necessary information that a buyer needs to make a decision:

  • Pitch Deck
  • Product Demos
  • Product Deep-Dive PDFs
  • Mutual Action Plan
  • Case Studies
  • ROI Analysis
  • Pricing and Proposals
  • Security and Compliance

Buyers love deal rooms because it makes their life easier. Instead of digging through emails, buyers can just visit one link when they need something. These deal rooms support champions during internal conversations with stakeholders. Champions can simply share the sales deal room link with other people on the team to show the product’s value.

For sales teams, deal rooms give signals into the engagement level of the buying team. Analytics shows when buyers watch videos, download pdfs, etc. It gives the sales team insight into how the internal conversations are moving along.

Sales deal rooms also help sales teams build a repeatable process. Sales teams can set up a company template that standardizes follow up across the organization. These deal rooms give sales leadership teams centralized control and a way to make sure the sales team is sharing the best resources every time.

Sales deal rooms provide a methodology for Account Executives to be consultative. These deal rooms act as a collaborative workspace where AEs and buying teams can work together to drive alignment and move a purchasing process forward. They can collaborate on a project plan and share resources back and forth.

Lastly, sales deal rooms help AEs finalize deals. Within these deal rooms, AEs can share pricing quotes and manage the contract process.

Concluding Thoughts: The Virtuous Cycle of Enterprise Sales

The best companies connect the enterprise sales process to a customer success experience that’s equally tailored for bigger companies. AEs seamlessly pass off the relationship to the customer success manager (CSM). The CSM then runs the company through the implementation program – ranging from admin checklists to company-wide training and enablement programs to make sure the company is successful. The CSM should be doing everything they can to make sure they are happy customers who will be a referenceable case study.

The great thing about Enterprise sales is that it usually only takes one happy customer. Once you figure out a process that works for one customer, you’re able to repeat those lessons and acquire the next customer.

As you start to get more enterprise case studies, other enterprises will be more confident in your product. Sales conversations start to change. You’ll evolve from an up and coming SaaS startup to a legit software provider that helps companies around the world. The snowball will keep rolling downhill and you’ll close more and more deals.

Moving up-market takes a ton of hard work. But there’s no better feeling than starting to close big deals and watch ARR skyrocket.

  • Sign in
    Comment

New Report

Close