So you want to sell your software solution to large enterprises? Here are 7 tips from Citi Ventures.

Matt Carbonara

Global Head of Enterprise Tech Investing, Citi Ventures

Vibhor Rastogi

Global Head of AI Investing, Citi Ventures

Cagla Kaymaz

Principal, Citi Ventures

Large enterprises represent a massive customer opportunity for many B2B startups. While selling to Fortune 100 companies over small-to-midsized businesses (SMBs) or mid-market companies can mean longer sales cycles, more complicated contracts and additional tech considerations, it can also dramatically expand your product's impact, drive new product development and unlock substantial long-term revenue.

But how do you go about landing a large enterprise customer?

At Citi Ventures, we’ve invested in dozens of leading enterprise tech startups, introducing many to the stakeholders who control Citi’s $12 billion annual tech spend and guiding our portfolio companies through the complex enterprise sales process. In doing so, we have learned what it takes to build and sell software solutions to large enterprises — and we’re happy to report that with a bit of planning, some help from inside and a lot of determination, it can be done.

So, take a deep breath and read our seven tips for selling to Fortune 100 companies.

1. Understand your potential customers’ priorities before you build

Large enterprises often have varying internal goals and drivers, which can make it hard for them to align all their stakeholders behind bringing on a new vendor — unless that vendor’s solution addresses a top-of-mind pain point. So before you start building your product, do your best to make sure that it will!

If you already know what’s keeping these stakeholders up at night, great! If not, work to uncover their top priorities by listening to their earnings calls and interviews, socializing your product idea with them, etc. If you’re already selling to a different part of the market (e.g., to growth-stage startups), research the similarities and differences between their personas. That will give you the best chance of building a solution that large enterprises will want to put budget and resources behind.

2. Be enterprise-ready from the get-go

Becoming enterprise-ready is no small feat. Large enterprises, particularly those in heavily regulated industries like healthcare and financial services, often have significant compliance requirements, legacy tech stacks and other barriers to break through.

For example, startups will often tell us they're enterprise-ready because they have SOC 2 security certification, but many large enterprises require additional data security certifications like ISO 27001. If you’re selling into healthcare, are you HIPAA-compliant? Do you have documented policies and programs around data access and which authentication providers you integrate with? If not, put them in place: large enterprises will want to see them.

Building for large enterprises also requires deployment flexibility. While we love SaaS companies, certain enterprise applications (particularly those that deal with sensitive customer data) need greater security than cloud computing can provide. Be prepared for deployments ranging from virtual private clouds to on-premise (yes, that’s still a thing).

All these requirements can add significant cost and time to your roadmap, so before you start down this path, analyze the market and decide if the opportunity is worth the work your team might have to put in to seize it.

3. Don’t build a better solution—build one that's best-in-class

There’s an old saying in the corporate world: “Nobody gets fired for buying IBM.” Large enterprises tend to be cautious when it comes to adopting new tech, as buying a product from an “unproven” startup can bring increased risk of unanticipated issues and costs. To overcome the bias toward incumbents, your product can't just be slightly better than legacy solutions: It needs to be 10X better.

That means you will likely have to go beyond improving a user interface to win across several vectors such as integration and deployment, and/or leverage cutting-edge tech to address lingering issues from older solutions (e.g., using AI to build 10X better robotic process automation tools). Your product should also be able to interoperate with the enterprise’s existing infrastructure, making it as easy and impactful as possible for your customer to adopt it.

In other words, the cost-benefit analysis should weigh so heavily in your favor that onboarding your solution will be a no-brainer and an easy win for your customer’s decision-makers.

4. Hire your sales team earlier than you think

Don’t wait until your product is ready for primetime to hire your sales team; do it once you’ve achieved product-market fit, if not sooner. For first-time founders especially, we recommend hiring a seasoned enterprise sales executive who has sold to your target companies before—they will bring more of the network and know-how needed to penetrate the enterprise market than, say, someone from a company with a product-led growth motion.

5. Cultivate champions and sponsors within your target customer

Enterprise sales is all about relationships, and the larger the enterprise, the greater the need for key decision-makers like Chief Information Officers (CIOs) and Chief Technology Officers (CTOs) to champion your product. The best way to cultivate these champions is to get “warm introductions” from your investors, other customers and/or the enterprise’s strategic innovation or venture capital groups (our personal favorite method). By adding a corporate VC to your cap table, you will bring on an investor that is not only highly incentivized to help you succeed but also deeply ensconced within your target company.

6. Be prepared to prove (and prove again) your product’s scalability and feasibility

Large enterprises will want to know right away if you have scale of service that can match their own. If you are already working with a company of similar size and scope, let your potential customer know even if you can’t name names—it will help ease any concerns about your enterprise-readiness and provide “social proof” that your solution is the best one for them. If you have not yet reached that level of scale, lean into what makes your team qualified to do so. Did you build a distributed system at a large tech company serving millions of customers before starting your company? If so, say so.

Once you get your foot in the door with a large enterprise, be prepared for a lengthy onboarding and testing process. While you might be used to signing deals with SMB customers after only a product demo or presentation, that’s rarely the case for big corporates. Expect to do a proof-of-concept project that is both connected to a budget for the full deployment and aligned with the customer on what success looks like. This process can take months and is often unpaid, so you should account for that in your planning.

7. Land, expand and support

Signed the contract? Congratulations! Landing the initial contract is the hardest part of the job. Even if your first use case is of low contract value, make sure you deploy enough resources to ensure that it is a success and provides strong evidence of your value-add. That includes putting a top-notch customer support team in place: A great customer experience is critical to ensuring a successful long-term partnership with a large enterprise customer.

Once you’ve accumulated enough data points to demonstrate your solution’s ROI, look for other use cases within the same enterprise — it's much easier to expand once you are an approved vendor.

Selling to large enterprises can be daunting. However, as major customers that tend to have high vendor switching costs, they offer significant upside for B2B startups and are often worth the effort to pursue.

In doing so, it always helps to have a guide—a guide like Citi Ventures. If you’re building an enterprise software company and want some help along the way, reach out to us at, and!