7 Tips for Pitching and Winning Enterprise Deals

Stepping into the big league of enterprise sales is no walk in the park, especially for start-ups. With over five years under my belt managing a Data & Tools department at a leading CPG company and juggling a seven figure budget, I’ve seen my fair share of pitches from start-ups in the Marketing Tech and Research Tech spaces. From these encounters, I’ve picked up a mix of winning moves and common slip-ups when it comes to winning over enterprise clients. In this blog post I will share my experience of how the best startups nail enterprise deals.

1. The Maze of Enterprise Decision-Making: Don’t underestimate how complex the decision-making is in big companies. You’ve got loads of people to win over, each with their own agenda. It’s a game of patience. From your first pitch to the final nod, it can take ages to seek alignment amongst multiple internal stakeholders, so stick with it and keep nudging them along.

2. Tailor-Made and Scalable Solutions: Loads of start-ups miss the mark by not realising that big businesses need solutions cut out just for them. Flexibility in what you offer is key. Also, remember to focus on your product’s scalability and reliability. Bring out the case studies and stats to back yourself up. Nailing a pricing model that big companies will go for is key. Getting your demos spot-on, focusing on the specific challenges these big decision-makers face is important.

3. Security, Compliance, and Real Benefits: Skimping on security and compliance in your pitch is a no-go – these are biggies for big companies. Stick to standards like SoC2. Keep in mind regional regulations like GDPR, CCPA, etc.

4. Building Trust with a Solid Track Record: Breaking into the market and building trust is tough. Just flashing logos of big-name companies without showing the real impact you’ve made won’t cut it. Trust comes from proving your worth by showcasing successful partnerships that have clear client benefits. Sharing tales of your wins and introducing prospects to other clients in different industries can really boost trust. These real-world stories provide valuable lessons and insights for potential enterprise clients. It is better to showcase examples of real impact instead of flashy logos. Avoid showing logos of enterprise companies that are not current clients — this is a telltale sign that you may not be ready to manage an enterprise account.

5. A Crack Sales Team: Your sales team needs to be more than just good at selling; they’ve got to really get the complex needs and wants of big businesses. This means savvy strategic thinking, deep industry know-how, and the ability to understand and define the value benefit for the customer. And don’t just talk features – highlight the real perks and value your product brings to the table. This can either be in the form of savings or creating value.

6. Understand The Procurement Cycle: Knowing how big organisations handle their budgets and procurement is crucial. In my own experience, even with a big budget, there were rules, deadlines and a buying cycle. Getting to grips with these buying processes and compliance is a big piece of your sales puzzle.

7. What have I missed? Have your say!

One comment

  1. Great article, Ash! Another thing that startups can keep in mind is being prepared to tackle enterprise-level onboarding once you do win the deal. This might look like…offering a dedicated success professional, holding ongoing training sessions and refreshers, hosting office hours, providing ample video tutorials, conducting roadmap reviews, forming a customer advisory board, etc..

    It’s also worth startups having a plan for specific product features that can be important to certain large enterprises (especially those with multiple or regional teams): e.g. self-serve admin, group or folder organization, and the ability to provide usage audits.

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