AMA: Adobe Director, Adobe Sales Academy, Jessica Holmes on Scaling a Sales Team

Being the first sales hire at a startup is a unique opportunity—and a big responsibility! You’re not just selling the product; you’re helping build the sales function from scratch. If you’re stepping into this role, here’s how to make the most of it: What to Focus On First Learn the product inside out Because you are going to be the sales expert from both the sales process, as well as the product functionality, try to sit in on product meetings, use the tool yourself, and understand the “why” be ...Read More

Moving upmarket—selling to larger customers with more complex needs—is a major growth lever and very exciting! But, it’s also a shift that requires new thinking, new processes, and often, a new mindset. If you’ve been tasked with leading this transition, here’s some recommendations on how to approach it. Key Moves to Make Redefine your ICP: Enterprise buyers have different pain points, buying cycles, and stakeholders. You may find that Procurement teams within your prospect's organization are no ...Read More

Motivating a sales team isn’t static—it changes as your team grows and matures. What energizes a team of three won’t work for a team of thirty. The key is to evolve your approach in a way that supports performance, culture, and long-term growth. Motivation Strategies by Stage Early Stage (1–3 reps) High-touch leadership: Daily check-ins, direct access to leaders and product Celebrate small wins: Every deal is a milestone! Example: A simple way to celebrate wins is by having a Slack channel or em ...Read More

As your sales team scales, so does the need for clear, consistent communication with other parts of the organization. Here’s how to keep everyone in the loop without overwhelming them. Simple, Scalable Communication Tactics Weekly Digest Share wins, pipeline highlights, and key metrics Keep it short and consistent (Slack/Teams messages or email works!) Example: At a previous company, our “Friday Wins” email became the most-read internal comms— and really helped to build cross-team alignment and ...Read More

You're on the right track! What worked for your first 10 or 100 customers may not work for your next 100. The key is creating change in a structured way - and knowing when to make changes, and how to do it without disrupting momentum—is key to scaling effectively. Identifying Signs that it’s Time to Evolve Deals are consistently stalling: Especially at the same stage (e.g., proposal or negotiation) that may signal unclear value prop or pricing friction. Forecasts are consistently off: Big gaps b ...Read More

When your sales team is just one or two people, but your product suite is broad and technically complex, it’s easy to get stretched thin. The challenge is balancing short-term execution with long-term scalability. Here’s how I'd suggest you divide the workload strategically to support both. Short-Term Strategies for Managing Complexity Divide by Product Familiarity or Strength Assign each rep to lead on the product(s) they understand best. Let them own enablement, demos, and feedback loops for t ...Read More

Moving from a solo sales person to a full team requires more than just adding headcount—it demands structure. I'd suggest the following when expanding your sales team from one to many: Hiring Framework Define roles clearly - who is responsible for what in each sales stage and how they will work together Standardize interviews and scorecardsExample: At a startup organization, we implemented a structured hiring rubric that cut time to hire and ramp time by 30%. Onboarding Playbook Create a structu ...Read More