AMA: Adobe Director, Adobe Sales Academy, Jessica Holmes on Developing Your Sales Career

There are a few hard skills that are table stakes for any sales leader: Understanding Pipeline: you have to be able to read a pipeline, spot risk, and forecast with confidence. If you can't do this, you lose credibility fast with your leaders, sales ops, etc. Data Literacy: sales leaders need to use data to drive decisions - can you ask the right questions of the data and translate that information in to decisions and actions? Coaching Skills: multiplying the abilities and strengths of your sale ...Read More

A question I use often is: "Tell me about a deal you lost — and what you'd do differently" or if early in career, a question with the same sentiment: "Tell me about a time you failed - and what you'd do differently". I love this question because it tells me everything: self-awareness, coachability, how someone processes failure, whether they own their outcomes or externalize blame. In sales, we celebrate wins but how you handle a loss is really where sellers are built. We're told "no" more often ...Read More

This is something I think about a lot — especially given my role in building early-career sellers. Sales is always evolving, but today it feels like the game is changing fast! From my view, a lot of a seller's transactional and mundane work is being automated, and buyers are coming in more informed. The role of the seller is moving from delivering information to helping people make decisions. That means sellers require stronger business acumen, the ability to navigate multiple stakeholders, and ...Read More

When communicating with C-Suite or stakeholders, the message doesn’t change, but the translation does. With executives, you need to lead with the answer: what’s happening, why it matters, and what decision needs to be made. It’s about clarity and business impact. Lead with the "so what" — executives don't need the journey, they need the destination and why it matters to them Frame everything in business outcomes: revenue impact, risk, efficiency, growth — not activities or effort Use the "headli ...Read More

This is a question most sales leaders are actively wrestling with right now — because the honest answer is that nobody has fully figured it out yet. Here's my perspective: AI isn't a tool to bolt on top of existing process; it's a fundamental shift in what the job actually requires We need to think about AI in two layers: productivity accelerator (research, drafting, prep) and capability raiser — helping average performers get closer to what top performers do naturally Build AI fluency into onbo ...Read More

Here's what I wish I'd known earlier in my career: Your reputation is your longest-running asset. How you show up, how you treat people, whether you do what you say you're going to do - all of this follows you everywhere and will be what sets you apart. Get comfortable being bad at things faster. Being in sales, and especially tech, the learning curve is steep and public. The reps who accelerate are the ones who aren't precious about looking inexperienced, they're eager to learn. Ask the questio ...Read More

The combination of communications and economics is great because one (economics) really helps you understand how businesses work and make decisions, and the other (communications) builds your storytelling and influence skills. When you put those together, you become powerful in your ability to understand your customers with a compelling case and be able to deliver that through the vision of how you can help them. As for breaking into business development/sales, I'd suggest you focus ways to buil ...Read More