Driving Sales Velocity in Complex Enterprise Deals

Mark Vashon
Mark Vashon
Mark Vashon has led sales at major enterprise software providers including AgilOne, SuccessFactors and ServiceMax. In this guide, he describes how startups should navigate the varied stakeholders, established processes, and long sales cycle that comes with enterprise selling.

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Questions Covered in this Guide

What are the key ways complex enterprise deals are different from more transactional sales?

You tailor the sales process  to them – the big difference about enterprise versus SMB is you’re going to tailor the way you go through a sales cycle to an enterprise deal based on the people, the product, and the industry they’re in, and how they buy software today (not  the sameselling process that you always go through).

Internally, they probably have some processes for evaluating software vendors – they’ve been down this road many times. They’re going to be focused on the business value, the viability of the vendor, some set of specific requirements, and the compatibility of the software. Then, they’re also going to look at multiple vendors, not just one or two.

Different departments care about different things – you have to recognize that there are different personas with different agendas involved. You have to understand what is important to each of them. 

Politics are important – you need to look for “the mole” who can help you understand how things work on the inside of the prospect’s organization, not just how it works from the executive’s perspective. You need to triangulate the account to develop multiple relationships.

When selling specialized enterprise software, you often have fewer “at-bats” in the market. How should teams maximize each opportunity?

Invest more deeply in each account

  • Read press releases, public company filings, set Google Alerts, research Linkedin, analyze their competitors to understand their industry company.  
  • Analyze their organizational hierarchy to identify key stakeholders
  • Figure out the competitive solution landscape and develop a differentiated strategy

Show that you do bring value – you want to educate, build relationships around providing value, and educate yourself about their business. Once you establish good credibility with the key evaluation team they’ll talk to you and take your calls and respond to your emails. 

Play to the long game and stay in touch – just send a quick note saying, “Hey, I ran across this article last week and I noticed this one thing in here. I thought you might be interested.” That’s all you have to do. 

What are the roles that might be involved in a complex sale on your company’s side?

The salesperson shouldn’t be the only point of contact – let them get to know you from multiple angles – and build interpersonal relationships with different members of your team. Throughout the sales cycle, they’ll meet more people and they’ll just feel better about your company and the ability to support them.

Leverage the goodwill the sales development rep (SDR/BDR) built – this is the person that, in an enterprise situation, calls the prospect for months and months, along with sending emails, webinars that you’re hosting, or press releases. It can’t be overstated how much an extremely effective SDR can get done.

Use a solutions engineer to build technical relationships – this person brings subject matter expertise. Have the SE figure out who in the group is going to influence the buying decision from a technical perspective or requirements perspective. That way, you can focus on the things they really  care about. 

Introduce implementation early – I like to introduce the implementation process and the people who are going to own the implementation early because the prospect needs to know how they’re going operationalize   the software they’re buying

Bring in execs strategically (especially if you’re early stage) – bring your CEO in at the right time, to the right person to say “you’d be a strategic partner for us, and we’re going to make sure you’re successful”. You can also get your VP of Customer Success on the phone. It only takes 10-15 minutes to say “here’s what we are going to do to make you successful.” 

How do you make sure Enterprise SDRs/BDRs can handle big accounts?

Promote your best BDRs up to enterprise – have your new hires cut their teeth on SMB, but promote your rock stars up to the enterprise as soon as you can.

How should AEs and SEs work together?

Every good AE should have solid product knowledge – every good AE should know how to pick up the product and do a demo on their own. They should understand the primary use cases and the business value associated with those use cases and be able to walk through the product. 

Let the Solutions Consultant do their job – AE’s should not provide running commentary on the demo “could you show this, you need to show that”. Instead, coordinate in advance, do a dry run and define the roles. For each presentation, they should spend time to agree upon the use cases and workflows, based on the discovery data.

What are some of the roles you’re likely to encounter on the buyer’s side (e.g. the champion, more senior execs, procurement, etc.)?

The CEO (maybe) – I’ve sold millions of dollars of software and never talked to a CEO and I’ve also worked at some companies where getting the CEO was the smartest thing that we could do because we couldn’t get the deals done at the VP level.

The business owner and/or the champion – the business owner is the person who is going to get the most benefit from the solution, e.g. a VP. The champion is the one that’s going to get the deal done. The champion may or not be the same as the business owner or at the same level within the company, but they have the right influence.

The administrators of the system – if it’s a back-end system, the people who’re going to manage and own the system are really important to sell to. For example, if you’re selling an expense management system, you need to talk to whoever is reviewing expenses today. If they validate that your solution is worth it, it’s going to be much better.

The heavy users of the system – in the expense example this might be the business unit owner who has to approve a bunch of expenses. For them, this might not be a mission-critical app, but it could help save a significant amount of time. So in some cases, you would go to the end-users to see if you can find ways to improve upon their current system.

How should you think about managing multiple decision-makers and signers?

Ask the right questions to uncover other departments who need to sign off – ask, “who else needs to see this? When’s the last time you bought software like this, who was involved?” You’ll likely need:

  • Procurement – to agree to terms and conditions around cost and payment
  • Legal – to look at the contract
  • IT – to confirm compatibility and integrations
  • Security – to approve security specs
  • Board if the company’s process requires board approval

Motivate your champion – you’ll need your champion to make things happen inside their organization, and they’re going to ask you to concede on things you don’t want to do.  Build a relationship with the champion, and give them things that they need to get the deal done even if it’s inconvenient for you.

How should you think about partnerships in enterprise sales?

A partner likely can’t sell your product for you – if you’re selling a complex product to a big company, it’s rare that your partner is going to know the product as well as you do and represent it the same way you would. Plus, they’re always going to sell their offering first.

Implementation and integration services partners are common – there’s a good win-win when software companies don’t want to do integrations.

How can you accurately forecast and manage a pipeline of lumpy enterprise deals?

Sales leaders should ask questions about value – to get a feel for whether the prospect will really buy

  • Why do they need to buy this product?
  • What’s the problem they’re trying to solve?

Sales leaders should keep tabs on key stakeholders and compelling events – to have more confidence about the buying timeline.

  • Do they have a date where they want to go live?
  • Have they told us their selected vendor?
  • Have we started the contract process?
  • Have they talked to references yet?
  • Have they shared internal business care?
  • Is the project approved internally?
  • Have they agreed upon actually completing the transaction by this date?

What are the most important pieces to get right?

Make sure that you align yourself in the organization with the influencers – build interpersonal relationships with the folks who can highly influence/make the decisions. 

Tie everything to the business problem – the AE should always know what the top business problems the prospect is trying to solve with your solution and continue to tie everything that you’re showing back to how you can solve the business problems.Most importantly the individuals you are working with won’t share the same perspectives related to value

What are the common pitfalls? 

Beware competitors – don’t forget that there are almost always competitors on the scene, some of whom are known-commodity incumbents. If you’re trying to get more touchpoints or introduce your CEO and they say “oh, that’s not necessary”, that’s a big red flag. 

Don’t lose sight of what’s going on in the account – over a long sales cycle a lot can change. Financially, the company could have a bad quarter and no longer be in a position to buy. From a people perspective, key stakeholders could have come in or left. Don’t assume what was important months ago is still at the top of the list.

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