Startup Sales and Marketing to the Enterprise: "Old School" Meets "New School"

There is a lot of attention on “lean startups” and “scaling big” with minimal marketing and sales efforts. These are great stories and I love reading about the breakout, viral success of a hot startup. But that doesn’t reflect what the majority of startups experience and it’s even less frequent for one selling B2B software.

Let’s face it; selling B2B software is complex stuff. There are sponsors, blockers, administrators, users, and other personas at play. Initiating a sale can begin with any one of them. But to sell high-ticket, enterprise solutions at scale, you will need a systematic approach that can be applied by a sales team or channel.

The rise of SaaS/cloud-based products does mean that line-of-business purchasers are less IT dependent than when there is a hefty on-prem component. That’s good news.  However, many hosted products do need to integrate with existing systems in some fashion and will require some sign-off from IT and others in the org.

At the risk of making a sweeping generalization, people in the enterprise tend to fall into two buckets: “above the line” and “below the line.” Both are critical to running the enterprise, but they have different roles in the selling process.

Above the line people are executives, line of business leaders, and the very senior IT folks who set organizational priorities and allocate budget. They are more likely to take risks to move the organization ahead. No decent-sized deal is getting done without support from above the line – or by at least showing irrefutable evidence that your solution is directly tied to solving pains above the line. As the saying goes, "no pain, no change." They want to understand benefits, not features.

Below the line people are managers and their teams. They are accountable to execute projects that support the goals that were set above the line. These folks are also critical, because they will recommend –or veto– specific solutions and supporting projects. They will also seek out solutions to problems they have been given. It’s a big mistake to discount people in your database that don’t carry an exec title, as they can be instrumental in getting a deal started or approved. You need to serve them appropriately.

When selling bigger ticket B2B products that will involve a range of personas, I think it’s helpful to consider a two-pronged approach: top-down and bottoms-up.
  • The top-down approach involves “calling high” above the line to uncover high-level organizational objectives, pains and exploring ways the solution can help.
  • The bottoms-up approach involves reaching below the line influencers.  Enterprise sales efforts can benefit from ensuring that this crowd will approve a solution when asked – as well as considering it a place to start. In fact, many of today's B2B products sold into the enterprise are growing quite well by staying primarily below the line.


The CEO of GoodData, Roman Stanek, did a nice job of exploring the challenges and benefits of applying traditional “old school” selling techniques to reach the enterprise. It’s definitely worth a read.


He did a great job reminding the reader about the hard work of selling enterprise technology.
If you want to sell your technology to the enterprise, and buy a big ski chalet in Switzerland, you have to solve real problems for the enterprise, and you should expect to have a substantial sales and marketing operation. Fundamentally, the product has to make work easier, integrate better with other systems, and meet much more stringent requirements than a consumer product would. The enterprise is a large and slow-moving but a powerful and valuable animal. Capturing it requires addressing its concerns and its persona head-on. 

What he didn’t cover as much, and worth considering, is how applying “new school” techniques can assist selling into the enterprise. Inbound marketing tactics, such as content marketing, blogging, and social media, can in fact help earn interaction with target segments and drive people to engage.

CxO’s don’t generally try products, but below the line people value a product that is easily evaluated and an experience worth sharing. They have been significantly impacted by their experiences trying consumer-based technology in their personal lives. This is a real opportunity for marketing to drive engagement, trials and potentially even initial purchases when kept below procurement thresholds. Engaged users are a powerful feeder into the sales process.

If your product aspires or requires more widespread enterprise-wide deployment, a laser-focused sales team can help. But in this case they’ll be working to upsell happy accounts or to close bigger enterprise deals. More traditional selling techniques, such as outbound calling or telemarketing, may be helpful in supporting this too, but working from some base will always be more productive than raw cold-calling.

Many startups and early stage companies targeting the enterprise should consider applying lean startup discipline to a mix of new school go-to-market techniques with some old school selling.  The skill and art is determining the right mix!