AMA: Shopify Senior Team Lead, Retail Product Marketing, Courtney Craig on Sales Enablement

* Survey your sales reps quarterly or biannually on the effectiveness of the sales enablement materials/programs * Listen to sales calls to hear how prospects are reacting to what the sales rep is saying/presenting - are there objections that could be better handled? Could the pitch be refined? Do the prospects get hung up on pricing? * Audit the buyer journey as if you were the buyer. Once you are in the purchasing stage and talking to sales, can the sales reps provide the materials and answers you'd be looking for as a buyer? * Gather closed-lost reasons/a report and make sure Sales is enabled to battle the lost reasons * Look at your sales team's win rate over time - has it improved since implementing new sales enablement programs/materials?

Simple - always say yes to the needle-movers, and only do the one-sheets and other work if you/your team has time. PMMs shouldn't spend a significant amount of time on anything that isn't used frequently or won't move the needle. If you find yourself having to say yes to one-sheets frequently, then create a repeatable template where text and images can be easily swapped out by PMM or even a sales rep, and new one-sheets don't require a designer or copy writer. Depending on the team, Sales reps could be enabled to use messaging frameworks, image folders, and feature briefs to create one-sheets themselves.

I like to start by: 1. Interviewing and/or surveying the sales team on needs/wants. 2. Listening to sales calls - how are they pitching? What are they using to pitch? How is it resonating? 3. Audit for the basics: Can sales speak/show how we compare to competitors? Are the top objections and responses documented? Is there an up to date pitch deck? Is there any/enough social proof the sales team can share with prospects? 4. Prioritize what will improve the sales pitch first, then what you think will be used the most by Sales, then work down the list from there.

Sales team surveys! I love surveying sales teams quarterly or biannually on market trends, common objections, toughest competitors, most wanted features, top pain points, what messaging is resonating most, etc. I like to make most questions open-ended to get ideas, but if you have a big sales team you can create multiple choice answers. Another good thing to throw into the survey is a question about the effectiveness of the current collateral. This one I like to make multiple choice or as a scale/score, so I can measure improvements to this score over time.

I think they way we currently do this at Shopify is the best I've seen at a larger company, and it has three things in common with the best I've seen for this at smaller companies: - Dedicated time is set up to train sales reps on the new materials, especially if it's for a new feature/product launch, new pricing/plan, new campaign, new pitch deck, demo or event. (Break into groups if needed). - During those sessions, there is ample time for reps to ask questions and even practice playing back what you want them to communicate with customers. - The adoption and effectiveness of the new materials are monitored closely by PMM, and a sales feedback loop is created. - Sales feedback is taken seriously, and regular check-ins between PMM x Sales occur.

After the discovery call, if the prospect is a good fit, I like the sales rep to follow up with a more in-depth demo session, where they personalize the demo to the prospect's business needs. The outline of this demo can be created by the rep taking notes when they are on the discovery call. Then on the next scheduled call (or the rep can record a video), the rep actually goes into their demo environment and uses the outline to take the prospect through features/uses cases that interest them most. This takes a little time and you need to have a good demo environment set up, but in my experience it goes a long way.

Survey the sales reps quarterly or biannually, and include questions around which materials they use the most. Use multiple choice for this question, and leave a write-in line for feedback. You'll get direct feedback in a scalable way, and also notice trends over time.

Tell them you want to sit in in order to prepare better sales enablement materials for them for future calls, including objection handling documents, pitch decks, feature one-pagers, pricing calculators, and social proof. Tell them you will take detailed notes on what prospects ask for/care about, and tailor future materials to better address those things. This will save Sales lots of talking and provide a better tool box for scaling their own strategy.

Find ways to make it interactive. For example, if you are training them on a new pitch deck, ask a well-respected sales rep, coach, or the sales team lead to actually do a real pitch with the new deck during the enablement session. The reps will pay attention to how another rep makes a pitch/uses a deck. Or, if you are leading a roadmap enablement session, ask reps to share which customers requested these features and why before diving into the benefits of a feature. This gives context on the customer pain points and makes the enablement session stronger.

In smaller settings, asking sales to playback what you've enabled them on helps reinforce enablement. Ask them to practice explaining a new feature to you or giving you an elevator pitch on your product product. To reinforce efforts more broadly, make sure you have measures of success in place for your enablement efforts. For example, asking sales reps to record their sales calls when they are using a new pitch deck. Or, send out a sales survey after a new product launch to follow up on what's working/what's not from a messaging perspective on prospect calls.