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First Large Deals: An Enterprise Sales Reading List Ashley Dotterweich

Somewhere along the way, scaling deal size becomes essential to growing your business. But few (if any) enterprise deals land in your lap effortlessly, and effective enterprise sales requires a a strategy designed for larger deals. Raymond Colletti, VP of Revenue for Codecov, shared his advice on closing first large deals in a group workshop with Heavybit accelerator members. Ahead of the session, Raymond shared his required reading (and listening) for closing your first large deals.

Enterprise Sales Reading List

1. 4 Lessons From Selling Enterprise Software, Bowery Capital

This quick read from the Bowery Capital team shares 4 foundational lessons from selling enterprise software that the team has learned from working with portfolio companies. Learn about enterprise sales tips such as using proof of concepts as a sales tool and how to set up internal sales infrastructure effectively.

EnterpriseReady Podcast

The EnterpriseReady podcast is a great resource for all things related to building products for the enterprise, but Raymond highlighted three episodes in particular for their sales insights:

2. Ep. #1, Delivering Software that Enterprises Love with Chef’s Adam Jacob

Startups often consider enterprise customers as a sort of endgame — something you work up after nailing smaller markets — but market demand can surprise you. Chef founder and CTO Adam Jacob discusses leaning into enterprise interest sooner than he anticipated, and how he leveraged those early enterprise users as design partners to build a better enterprise product.

3. Ep. #2, The Early Days of GitHub with Tom Preston-Werner

While Github might be better known as a free-to-affordable platform for open source projects and early-stage startups, over half of Github’s revenue comes from large enterprise deals. In this episode, former CTO/CEO Tom Preston-Werner shares how Github grew into an enterprise solution. Listen for insights into topics including how to approach initial conversations with large prospects to how to design “delightful” experiences for enterprise users.

4. Ep. #5, The Evolution of Enterprise with Edith Harbaugh of LaunchDarkly

In this episode, LaunchDarkly founder and CEO Edith Harbaugh discusses how the rise of SaaS changed the way enterprise organizations buy software, and why this means enterprise-focused startups need to think about “the bacon” when designing product experiences. Edith also shares her thoughts on how to navigate selling to developers who think they don’t want to talk to a salesperson, but actually do.

5. a16z podcast: When Organic Growth Goes Enterprise

Bottom-up growth is more typical of consumer companies, but there’s been a shift in recent years towards applying this go-to-market strategy to enterprise companies as well. In this episode of Andreesen Horowitz’ podcast, a16z General Partners Martin Casado and Andrew Chen, and Russ Heddleston, CEO and co-founder of DocSend, discuss what a bottom-up approach for enterprise looks like.

Russ shares his experience at DocSend including how they knew went it was time to start building a sales team, how they prioritized and synthesized customer requests into new features, and how they thought about pricing and packaging for enterprise.

6. In SaaS sales, it’s important to play the long game. It’s worth it., HelpScout

This article from HelpScout stresses the importance of thinking about the sales cycle as a long process — even if it’s sometimes longer than we’d like it to be. Check out their real-world example of a single deal’s timeline, from the first conversation with a prospect to setting an onboarding date, to get a better sense of the daily grind of closing a large deal.

7. How to Start a Series A Fundable SaaS Business, ThinkGrowth.org

In this guide, angel investor Matt Ward lays out everything startup founders need to do to lay the foundations of a fundable SaaS business.

Raymond specifically calls out Part 2, “Retaining Customers”. This section tackles one of the biggest problems that SaaS startups face — customer churn — head on with some tips for keeping customers happy and engaged.

8. How to Execute a SaaS Land and Expand Strategy, SaaSX

“Land and expand” is a common sales strategy for SaaS companies, but it can be hard to actually pull it off. In this post from SaaSX, dive into what land and expand really looks like, and what team members and processes you’ll need to execute it successfully. Don’t miss the section on KPIs for land and expand strategies.

9. Big Deals, YCombinator

Founders often fall into the trap of believing that a single “Big Deal” will automatically create a huge, successful company. In this article, Aaron Harris shares common reasons why companies often fail to close big deals, and how they can take a better approach.

Learn More about Enterprise Sales with Heavybit

If Raymond’s reading list has piqued your interest, check out more content on building an enterprise sales strategy in the Heavybit library.

Want to learn from industry experts like Raymond? Check out Heavybit’s events calendar for the upcoming speaker sessions focused on sales, marketing, product, and management strategy for developer and enterprise startups.

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