AMA: HubSpot Director of Sales, Sarah Mercedes (Osborne) on Deal Strategy

Three things come to mind here: There needs to be pain in order to position a change. Ideally, identity pain (a personal challenge this person faces due to current state), process pain (a process that isn't going well due to current state), and business pain (a negative business impact due to current state). In this particular case it will be tough to get traction without identity pain or business pain, unless the business pain is extremely severe and unable to be solved for with the incumbent. ...Read More

The best way to increase your chances of winning the deal and shortening the sales process is to multi-thread key stakeholders at the onset of any large enterprise deal. There are 3 power levels you should be looking to be connected with for all large deals: The End User: If end users are not on board, derailed sale. Don't underestimate the end user. Manager: If manager not on board, challenging to onboard and drive adoption. Executive: If exec not on board, can/will veto the purchase. But if al ...Read More

First, you need to be clear on where your product wins and then match that up against where your competition's product is weak. Focus there. In my experience, when in this particular scenario, the intangibles can go a long way. Below are a few that can be very meaningful in an evaluation against a legacy product, when applicable of course: Product Innovation- Legacy products can be notorious for not investing in future product development, including UI/UX. Is that the case here? Is your product, ...Read More

This varies company to company, industry to industry, deal by deal, etc. but a recommendation I'd have is doing some discovery around this process with your POC up front, so you can plan our your quarter and forecast accurately: Tell me about your legal and procurement processes and the steps involved. How long does each step typically take? What typically matters most to your legal and procurement teams? After a couple of rounds of redlines back and forth, is your team typically open to getting ...Read More

Closing Plans are KEY. Getting to vendor of choice decision is typically 50% of the process. You need to understand up front exactly what needs to happen from VOC to signature, both internally and externally. For example, you may still need to present to their Exec Team for final approval, but your POC may also need to have a budget approval meeting internally and that Exec Team may then need to get approval from the board, who happens to meet monthly on the 3rd Thursday of the month. Once those ...Read More