Many businesses want to sell into large corporations, such as banks, asset managers and hedge funds, to boost their growth and user adoption. While large enterprise sales can certainly be profitable, unique skills and different tactics are required to successfully win large deals.

Recently I discussed how to be successful at enterprise sales with Mark Birch, Enterprise Sales Executive for Stack Overflow, a leading provider of knowledge sharing and collaboration tools for technology development teams.  Mark also founded the Enterprise Sales Forum, a community for B2B sales professionals to share, learn, and network with industry peers. Here are some gems from Mark’s 20+ years of experience selling to large institutions, many in financial services.

  • Leader: Mark Birch, Enterprise Sales Executive for Stack Overflow (@marksbirch )
  • Company Overview: Stack Overflow is the world’s largest developer community, bringing together over 50 million developers to learn, share their knowledge and build their careers. Mark is responsible for selling a private version of Stack Overflow’s knowledge sharing and collaboration tool to large enterprises with 500 or more developers so they can share information on their development processes within their technology development teams. (, @StackOverflow )
  • Enterprise Sales Forum: A community for B2B sales professionals involved in complex sales cycles. (,, @Enterprise_Sale )

LW:  What are the top 5 things anyone doing Enterprise Sales needs to know?

MB: First, they need to know how to communicate ideas effectively.  Second, be patient, yet persistent. Third, have an “other” orientation, which means the ability to appreciate other’s situation outside of yourself. Fourth, it’s important to have an intrinsic internal motivation to try new things and always be interested in improving, otherwise known as having a “growth mindset.”  Finally, be willing to do the work.  Learn about your industry, who are the influential people and what they care about.

“Many people selling to enterprises struggle most with finding the balance between persistence and patience.  Enterprise sales is a long game and you need to find the right time and people to connect with.  If your solution can’t add value in the near term, you need to recognize that your big idea may not be a priority for them right now.”  Mark Birch, Enterprise Sales Executive for Stack Overflow

LW:  What do people misunderstand most about Enterprise Sales and what should they know?

Stack Overflow’s Cool Office

MB:  Enterprise sales requires you to go “broad and deep” – it’s important to engage significantly more people because no one person makes the single decision.  You would want to foster relationships with the following key individuals:

  • Executive Sponsor: holder of the budget and approval
  • Influencers: provide input and suggestions
  • Involved Parties: others engaged in the selection process
  • Internal Sponsor: key contact shepherding the project along and selling the idea inside the organization.

LW: What factors affect the length of the deal cycle?

MB:  There are many variables that come into play, starting with the budget cycle. Every organization is guided by their process and bureaucracy.  Certain businesses require a greater level of scrutiny and have multiple approvers, particularly when more than one business unit is involved.

LW:  What tips do you have for startup founders who want to sell into large enterprises, like banks?

MB:  I think there are a few key skills that are needed:

  • Founders need to learn how to encapsulate what they do in an easily consumable message and convey why their solution matters
  • Know who your ideal customers are and more specifically, the different personas within companies. What do they care about and how are they affected by your solution?
  • Learn how to prospect both low and high in companies.  Can you have a value-driven conversation with the C-level?
  • Understand how large organizations operate within a complex organizational structure
  • Know how to negotiate, so that you protect your IP, deliverables and margins.

Mastering the sales process is critical to successful growth.  Learn more about how to sell more effectively at our upcoming Sales Launch Lab workshop series.  If you would like to learn more about how we can support your sales team in increasing its impact, contact us to schedule a complimentary strategy session to discuss your business objectives.