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Rebuilding Startup Culture for Enterprise Sales

The prevailing culture within startups jeopardizes their ability to sell to enterprises.

Rebuilding Startup Culture for Enterprise Sales

The prevailing culture within startups jeopardizes their ability to sell to enterprises. Anti-patterns:

  • Belief that the superiority of the product is the primary factor in market success, leading to an aversion or rejection of sales, marketing and other non-engineering functions
  • Narrow focus on early adopter audiences (i.e., indie web devs, other startups); related lack of empathy for other customer and user types
  • Inability to broaden and re-contextualize techniques used in organic growth and adoption (i.e., open source community building) to enterprise sales and marketing
  • Difficulty communicating effectively with users in a much larger and different organizational structure

The resulting impulse is to functionally isolate the people involved in production (engineering, product) from the people involved in distribution (sales, marketing). Unfortunately, success of enterprise sales is profoundly shaped by cross-functional work, communication and empathy. In this post, we look at some of the defining cross-functional competencies of startups that successfully sell technical products to enterprises.

1. They have an efficient supply chain for getting technical knowledge to the customer.

The ways enterprises evaluate, deploy and operate technology presents a level of complexity that makes consistent, timely and accurate delivery of information to them very difficult. These processes may be carried out across numerous departments, subject to changing organizational dynamics, and involve many people with no direct contact with the vendor. People involved in the buying process often have unpredictable and wildly varying levels of knowledge, even competence.

Building an efficient process for triggering and flowing technical information to customers is critical for enterprise sales:

  • Audit how technical information flows to customers during various stages of the sales cycle. This begins with a potential customer’s first contact with your brand, and extends to the lifetime technical success of the customer — i.e., communicating changes to products, discovered limitations and best practices, etc. Where is information missing, undocumented, inaccurate, difficult to find, or not reaching users and decision makers?
  • What are the most frequent problems caused by poor technical communication? Tracking support issues and common implementation errors are a great place to start. What knowledge gaps can we identify in our customer and prospect base and what are the root causes?
  • Sales teams invariably find themselves fielding questions beyond their technical depth. When technical issues must be escalated, particularly in the pre-sales process, is there a clear path and ownership for resolution?
  • What opportunities are you providing for people inside the customer company to get trained on the product? RTFM is a meme because people don’t. When you’re trying to sell products, this becomes YOUR problem. JIT documentation is often too late. Knowledge transfer means more than good docs.

Not having an efficient flow and feedback loop for technical information results in lost deals, failed implementations, and frustrated and misinformed customers.

2. Engineers talk to customers.

Inevitably, there are organic conditions that force engineering teams to make transformative contact with enterprise customers — such as production outages, bottoms-up deals, and big-ticket evaluation cycles. However, the culture often rejects and disincentivizes such contact as a normal occurrence. The mythology that engineers lack the social abilities to communicate with customers or cannot be trusted with them is not only inaccurate, but provides a cover for much deeper cultural dysfunction. Connecting startup engineering teams with enterprise technologists builds empathy for customer pain points, understanding of the implementation environment, and opportunities for high-value product changes:

  • Have a rotating schedule for involving engineers and product managers in early, mid- and late-stage sales calls. This schedule does not have to significantly disrupt building time — a few meetings a month can significantly increase understanding of the problem space.
  • Try rotating engineers through support cycles for 1-2 weeks at a time. While this can be disruptive to engineering work, the gains in empathy, understanding and knowledge sharing with customers and support staff tends to make it worth it.
  • Create ambient customer awareness by publishing customer notes , insights and data to the entire company — make it a cultural expectation that everyone reads and absorbs this knowledge and participates in the conversation it sparks.

3. They recognize the importance of professional services.

Our industry has been transformed with the rise of as-a-Service, the low-touch sales model, and the consumerization of the enterprise. However, these changes can be overgeneralized from a delivery model, software design or aspect of the full value chain into a cultural value that reviles high-touch, human-to-human value exchange. Outside of building a revenue stream, professional services:

  • helps build the trust and personal relationships that are required for large sales deals to go through
  • ensures that customers can extract the full value from the software because they are trained on how to use it and have had professional help in setting it up
  • can help customers navigate periods that are extremely risky and critical for current and future sales, such as going into production, an important migration, a capacity build-out, or introducing the technology to a new team

4. They build community with customer companies.

Community-building is instrumental in the success of many software companies as they build open source adoption and momentum in the early adopter segment of the user base. Many companies, especially those with open source or low-end products that supplement the enterprise business, can struggle to build the same type of community within enterprises — even though community there is equally critical for building trust, reputation and adoption. Here are some approaches:

  • Do hackathons, tech talks and meetups at customer sites
  • Invite and promote open source contributions from large customers
  • Create opportunities through conferences, dinners and meetings for groups at customer companies to meet and build relationships with your employees
  • Don’t fall into the trap of nurturing one champion within a large company, only to be in a tough position when that champion is promoted, leaves the company, or onto other projects. Make sure to build a community of champions with multiple individuals at a customer company for a more resilient business.

5. They understand, and are honest about, the technical aspects of their product.

Many enterprise software startups struggle with (unintentionally) misleading potential customers about their product. This can turn into cancelled contracts, burnt bridges, dissatisfied users, and draining support burdens. Building a company that is able to communicate often nuanced technical limitations and tradeoffs (see: the NoSQL market) is critical for a healthy enterprise business:

  • Sometimes, sales people don’t understand basic limitations of the product, fail to understand the severity and delicacy of technical subtleties, and accidentally mislead prospects. This can be minimized by cultivating a technically literate business team.
  • Having a technical partner that is closely involved in the sales cycle ensures honesty and accuracy in customer communications and generally reduces the duration of the sales cycle when selling high-tech products
  • Marketing should be required to get sign-off from the technical team on assets, messaging and collateral to prevent disseminating inaccurate information
  • Actively discuss and seek to document limitations of your product. Limitations will be discovered and change as your grow — a commitment to being open about them with customers is the critical factor


Enterprise sales is both extremely difficult and extremely lucrative for startup technology companies. Unfortunately, many of our shared values and cultural norms jeopardize our ability to sell successfully to these customers. Building a company that succeeds in enterprise sales often means rebuilding part of the culture. Eventually and cumulatively, active development of the competencies discussed in this post can help transform a culture hostile or toxic to enterprise sales.