AMA: Twilio Senior Director, Product Marketing, David Esber on Sales Enablement

I'm fortunate to work with a great team of Enablement partners who are responsible for building our regular weekly sales updates. We all are inundated with regular newsletters, emails and slacks, assigned trainings, and vendor promotions – it's hard to cut through that noise. Thanks to these partners, we're continuously improving the ways we get important information in front of teams, while also focusing on highest impact/most scaled activities. The team has landed on a highly-scannable, predictable, and regular update that gets the most important and relevant details in front of the GTM team. Rather than regular sales enablement webinars, we've started creating shorter, more snackable video segments (in addition to written resources or FAQs) that can be consumed when folks have time and assigned/tracked within our sales enablement platform. This was a direct response to dwindling viewership on dedicated webinars. While tactics are continuously evolving, there are a few best practices I've learned: * Tailor content: whatever the content, connecting the update back to their day-to-day processes, ability to retire quota, or meet a customer need is an important part of the message (and should be highlighted in the scannable description). * Measure performance: email newsletter tools, sales enablement and intelligence platforms, and even Google docs have analytics. Use them to understand trends and when things like off, talk to sales folks to understand what's going on. * Enlist spokespeople: just like anything we market, social proof is valuable. Highlight sales wins using key collateral with interviews, spotlight great customer conversations, or ask sales leaders to promote highly-important resources to gain additional 👀.

One of the most important skills for an PMM is to tailor our content to the audience. Working with technical products like APIs, and recognizing that our buyers and users are often different people with different technical levels means our product launch training also has to address those differences. Like most teams, we use sizing to dictate the level of effort of each launch and release by stage. Ideally, ahead of any significant launches we host live trainings at globally-friendly times for account executives and solutions engineers focused on key product messages, market trends, positioning, and launch details. Those are also great times to roll out and equip teams on customer-facing collateral. For our solutions engineers who are more focused on the how and technical implementation, hosting dedicated sessions with product counterparts helps to ensure we're addressing different audience needs. Those sessions are ideal places to highlight things like API features, demo resources, and product limitations. All of these live sessions become useful on-demand resources that can be assigned in an LMS or included in new employee onboarding.

Guaranteeing every person the sales team uses "official" messages is a sisyphean task; when you step back to look at benefit vs. effort, it's probably not worth the effort. Instead, here's where I'd focus my time: * Tier new messaging/resource rollouts like you would any launch – focus time, training, and effort on the most critical resources. For that content, gain buy-in from sales leadership to enable every team, including pitch certifications, on-demand resources including videos of salespeople tailoring the content to specific customers. * Ensure the content is highly discoverable. Get in front of teams, join QBRs, highlight new content at SKO, and "promote" it within your sales tools to make sure it's easily findable by sales people who are juggling many responsibilities. If they can't easily find it, they're likely to assume it doesn't exist. * Provide guidance on "key" slides/messages at the beginning of the deck. We include a single slide on most decks that tells the why behind slides and highlights the most critical slides in the deck as guidance for how teams might customize the content. * Provide talk tracks that are customizable/focus on key messages rather than how you'd say it verbatim. Every sales person is different and no matter the role, every presenter has a different way of communicating ideas. Offer bullets with key messages and allow them to customize the talk track for each slide around those key messages. * Monitor sales intelligence tools for gaps in understanding – and partner with enablement and sales leadership to revisit content and trainings.

One of the best things we can do as PMMs is talk to customers; joining sales conversations is a great way to gain a better understanding of ICP, customer pain points, and market trends – but it's also only scalable when it's focused on high-value engagements, used to test new narratives or positioning, or conduct research that's used to improve foundational assets like positioning frameworks and canonical pitch decks. Our team focuses our energy on producing and refining those foundational assets, ensuring they're promoted and versions are updated through our content repository. With major overhauls or new content we also like to treat those as launches with dedicated enablement sessions or self-paced learning modules, recordings of peers mock delivering the content. We also increasingly use a guidance slide at the beginning of the deck to highlight "optional" vs. "required" slides. That's the first line of defense. When 1-1 support can't be avoided because it's an exec ask, a critical customer relationship, or a relationship you're trying to build, preparation is key. Nine times out of 10, that deal support still involves modifying existing slides into a more tailored presentation or conversation. That's where discovery comes in – whether it's through teams or as part of a dedicated voice of customer session, understanding the customer needs/pains/interests ensures the conversation is valuable for the customer. For those conversations, I like to spend the vast majority focusing on the ask, and spend a portion of the call answering questions I have – either by testing new content, learning more about the customer roadmap, or gaining additional knowledge about the industry. Feeding that intel back into those foundational assets means everyone hopefully benefits from the conversation (and turns an unscalable engagement into a scalable one).

Enablement partners, like PMM, are balancing the needs and asks of multiple stakeholders. They sit in the middle of lots of initiatives and priorities, just like we do. And, we both benefit from close partnership to deliver the best possible enablement, keep a pulse on the needs of sales teams and leaders, and ensure consistency of message. For major initiatives, we've found it's best to engage Sales Enablement as early as possible in a workstream, soliciting input on best enablement modalities and working with the team to time the content for a period of time when there are fewer distractions. For ongoing alignment, a weekly call between our teams allows both teams to surface new requests, prioritize, and ensure visibility into roadmaps.