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

There are countless ways to leverage AI for coaching, forecasting and call reviews and a lot of it comes down to the AI maturity of the individual and the company in terms of how well and how consistently it's leveraged for these types of activities. The way to maintain data privacy and rep trust through these efforts, in my opinion, is to use public data to feed your AI models (logged emails, recorded calls, rep KPIs i.e. win rates, similar deals in CRM, etc.). That way it's not an invasion of ...Read More

Pipeline coverage! It's not enough to say deals and dollars created will get us to our quarterly target as we need confidence that the deal creation is leading to real opportunities we can close. Close rate and prior performance are far too lagging to give confidence for future performance. To consistently achieve these pipeline coverage goals, it's key to ensure the broader team has awareness of what the goal is and the "why" behind it. It's also critical to have accountability mechanisms in pl ...Read More

We run a consistent program referred to as What a Deal Wednesday (WADW). Every week, a different team within our sales org takes turns sharing a full breakdown of a significant deal they recently closed. It covers the following: Deal Team Company Overview Deal Source Business Challenges & Goals How & Why we Won Key Learnings We have a NotebookLM where all of these write ups are collected, which is a great resource for new reps and tenured reps alike to pull best practices and search for ...Read More

A couple things: Whenever you can build an action that requires reinforcement into your standard operating model where it is just considered part of the day to day process, the more likely it gets viewed as a business as usual task vs. a cumbersome, additional chore. I'd look for opportunities to have pipeline hygiene updates become a part of your team's regular motion and ensure they are clear on why it's so important to have accurate. Leverage automation wherever possible. We have Automated De ...Read More

The first step in creating a strong hiring profile, interview process and ramp program is defining "what good looks like" for a top-performing AE at your company. This should inform everything. What our team did first was document out the roles and responsibilities of an AE (broadly bucketed into Creating deals, Progressing deals and Closing deals). From there, we aligned on the core skills that a rep needs to have and show up with consistently in order to meet expectations across each of these ...Read More