If your sales team has only one or two people responsible for covering multiple products with complex features, how would you recommend dividing the workload in the short-term so as best to support long-term growth and expansion of the team?

For complex features, I recommend flash carding like you're in high school and listening to successful recorded call. This can be on an individual basis or in a group zoom setting. It's important that every quota carrying individual has a script that they can easily access and commit the sales script + top objections to memory. You can also bring in Solutions Engineers for demoing best practices to ramp up newer individuals on the team.

This is a good, and interesting question. Like many of the other questions, answering this properly requires more context, so I'd ask that you DM me to find some time to chat.

A couple of questions that come to mind when reading this question include:

How similar or different are the ICPs for these two products? What are the ACVs of the products? How do their sales cycles compare? Are your product and marketing teams investing in both of them equally? Etc.

While many might know Vanta as automating SOC 2, we have many products that our sales team sells today, and all of those products are pretty complex (the world of compliance is about as subjective as it gets).

One thing that we've seen in asking reps to sell multiple products is that they're going to focus on the products that are easiest to sell, and the products that will make them the most money.

The art and the science here is being really thoughtful around pricing and packaging methodology, and also sales compensation incentives, so as to drive the results that you're looking for.

Once again, hard to answer this one directly without more context, so please reach out to me directly!

When you have a small sales team responsible for multiple products with complex features, dividing the workload effectively is critical for both short-term success and long-term growth. Here's how I recommend approaching this challenge:

Leverage Cross-Functional Collaboration:

• Partner with Internal Experts: Given the complexity of your products, it's essential to collaborate closely with your cross-functional partners, including co-founders, technical staff, engineers, and product managers. These individuals bring deep product knowledge and can provide invaluable insights during sales cycles.

• Curate an Ideal Sales Cycle: Work with these internal experts to curate an ideal sales cycle for each product. This involves mapping out the buyer’s journey, identifying key value propositions, and understanding how different product features align with customer pain points and objectives. Document these insights so that they can be easily referenced during sales calls.

Pre-Call Preparation:

• Comprehensive Briefing: Before every sales call, ensure that your team is thoroughly briefed. This preparation should go beyond simply outlining the agenda. You need to guide your team on how to perform on the call—what communication style to use, how to address the prospect’s business objectives, and which value propositions to emphasize.

• Define Call Objectives: At the beginning of each call, clearly establish the intended outcome. One effective technique is to start by saying, “My objective for today’s call is...” or “If I’m successful, by the end of this call you’ll be thinking, feeling, and saying the following...” This sets a clear expectation for both your team and the prospect, ensuring everyone is aligned on the goals of the conversation.

Divide and Conquer:

• Specialization by Product or Feature: In the short term, consider dividing responsibilities among your team members based on product lines or specific features. This allows each salesperson to become an expert in a particular area, making it easier to manage the complexity of your offerings.

• Rotational Coverage: Alternatively, implement a rotational system where each team member takes turns focusing on different products or features. This can help distribute the workload more evenly and build a broader knowledge base within the team, which is beneficial as the team grows.

Create a Knowledge Repository:

• Centralized Documentation: Develop a centralized repository where all curated sales cycles, value propositions, and product details are stored. This resource should be easily accessible to both your sales team and cross-functional partners, ensuring that everyone is equipped with the information they need for successful calls.

• Ongoing Updates: Regularly update this repository as new insights are gained or as products evolve. This dynamic resource will support your team’s ability to adapt and respond to changing customer needs.

Feedback and Continuous Improvement:

• Post-Call Debriefs: After each call, conduct a brief debrief with your team and any cross-functional participants. Discuss what went well, what could be improved, and how the call’s outcome aligned with the initial objectives. This feedback loop is crucial for refining your approach and improving performance over time.

• Iterate on the Process: Use the insights from these debriefs to continually refine your sales process and the way responsibilities are divided. As your team grows, this iterative approach will help you scale more effectively while maintaining the quality of your sales efforts.

Focus on Long-Term Growth:

• Develop Future Leaders: As your team expands, start identifying potential leaders who can take on more responsibility and eventually lead specialized teams. Invest in their development by giving them opportunities to manage complex sales cycles and work closely with cross-functional partners.

• Scalable Processes: Ensure that the processes you establish are scalable. What works for a team of two may not be sustainable for a larger team, so continuously assess and adjust your approach as the team grows.