AMA: Twilio Senior Director, Product Marketing, Vanessa Thompson on Sales Enablement

The best tool you can ever have is a great relationship with your sales leaders and super star sellers. Building empathy and truly understanding their challenges is critical to your success. We use Highspot as our knowledge base and document repository. It works well for us and each product PMM can own and update their own product spot, which makes it easy to keep content refreshed. We also use Showpad for the online training element.

I meet with someone in sales, in some capacity, every few days. Before I hopped into this AMA, I was listening in (live) to a roundtable discussion with some key customers hosted by a product leader. Even though I was in “listen” mode, it was great to hear directly from customers about what they are thinking and how we can solve their problems. The key challenges raised by our customers can directly translate into prioritization of where we spend our time enabling the sales team as well as the sales assets we create.

I encourage my team to be the ‘mini CMO’ for the products they cover. That means the single biggest metric to measure is pipeline (with a focus on pipeline generation). Depending on the specific in-quarter activities we have going on around sales enablement, we can see a dedicated focus on sales enablement and education show up in our sales-sourced pipeline in the trailing quarter. My advice here is to track a few things: Attributed pipeline = how are all your content activities showing up in your pipeline efforts, eBooks, webinars, etc. Sales-Sourced Pipeline = Did you focus on a specific and deliberate effort around sales enablement that you can tie to an increase in sales sourced pipeline around a specific product or use case?

I love this question, <3 Developers! The fundamentals of sales enablement dont change, it's more the way you communicate the needs of your audience to your sales team that changes. If we unpack developers and what they want, then it makes it really easy to figure out how to approach sales enablement. 1) Developers will question to the end. They will question every word on every slide and understand it as a direction or intention. So make sure that any presentation or pitch you build for your sales team is fully accurate and defensible. A developer will ask about every permutation of the concept you lay out so you need to educate and prepare your sales team to handle any random question that might come at them during a pitch. 2) Developers are the architects of ideas. Developers are often the masterminds of a new innovation or invention in a company. So you need to take them most of the way there. Can you make it super easy for them to find the information they need to start working with your APIs? Do you have an easy to clone github repo? Do you have a step-by-step tutorial for them? Do you have a demo video ready to go? Even if a developer does sit through a sales pitch, you need to give them a carrot so make sure that there is always an actionable CTA at the end of a presentation AND that the sales team knows how to answer any questions on the set up or even do the demo themselves. 3) Developers want to dive in - yesterday. If you announce something, assume it is 1000% ready to go because developers want to get their hands on it right away. If you are doing enablement around a product launch, you should make sure that you have a tight workback schedule and that your enablement happens well BEFORE your launch so that your sales team is empowered and educated to answer any questions that come up from developers.

We are heavily involved in the Sales Kick off so that's where we focused our time and energy. At Twilio, we break out Sales Kick off from the main Company Kick off so I make sure to participate in all the forums where decisions are being made as well as listen to my stakeholders (and listen to the data) about what they want to hear. I then ‘pitch’ the sales leaders creative ideas for how we can enable their teams as part of SKO. Early in 2020, my team worked really hard to produce two hours of programming as part of our Sales Kick off. Because of the empathetic approach, we had excellent feedback from stakeholders, “that is the best presentation from product marketing that i’ve seen at Twilio”.

Get out in the field as often as you can and meet with customers but also seek out the super star sellers and find out their secrets to success. Your goal should be to become a trusted advisor to the sales team. This means you have the ability to diagnose problems and challenges that the sales team run into and then make the right recommendations to improve their situation. Showing up and being in the trenches alongside them is the single best way to build your partnership with the sales team - it not only builds empathy but it helps build your knowledge of the challenges they face every day.

This is really dependent on your org, how big you are, and your overall coverage model. In general though, it's a partnership. I view the relationship with my sales enablement partner as one of the two most important relationships I need to build in the company (the other being product). You need to build tight alignment on what each team does and doesn't do. At the highest level, I think about the division of duties as an input and output model. We (PMM) work on all the enablement inputs, content, decks, objection handling, other assets and collateral, and the sales enablement team works on the output, i.e. execution and alignment with the sales team. The enablement team owns the enablement editorial calendar and the ultimate delivery to the field.

1) A (first call) pitch deck. This is a fantastic unifying asset that will help you hone your narrative and it can also serve as an educational tool for the sales team. You can use the pitch to walk through your logic and approach and then refine it based on specific feedback from your sales team. 2) A mid-funnel eBook. It might sound a little strange that this is on the line up so high, but now that we are all working from home, the selling cycle is a bit different. Leaving a prospect with something they can consume on their own time is critical to move the sales cycle along. The benefit for you as a PMM in building an asset like this is that you get to keep refining your narrative, while expanding on some of the specific benefits. 3) A two-page leave behind. This is an asset where you can focus on your value prop, customer benefits, and highlight the success of current customers. 4) A short and pithy internal asset that covers detailed discovery and objection handling. Starting the conversation can be the most challenging for a rep so giving them really solid evidence and empathetic discovery questions can give them confidence to ask the tough questions. 5) A high-level competitive landscape. Do you know the major companies you are competing against and why you are better positioned? It's never a good idea to get caught up in what your competitors are doing, you should always be focused on your customers. But it's good hygiene to know what gotchas to look out for from a competitive perspective.

There is a bit to unpack in your question here so i'll focus on the product release element. We ‘size’ each release and the associated size determines a list of activities for that release. We use tee-shirt sizing so as an example, if a release is defined as a Large (where we go from S to XL), then a product release has a big revenue opportunity and we will complete a number of major initiatives: 1) Standalone AE enablement. We don't typically do standalone enablement that is outside the regularly scheduled monthly enablement so it's a big deal when we do it. This launch needs to impact every rep so that they will pay attention and educate themselves about your new release. 2) Explainer video/demo. If you are getting primetime with your new launch, then you need to make sure you cover as many mediums as you can. Demo and Explainer videos are a key part of enabling your team. Some pay attention to presentations, or collateral, others to videos. You should cover all your bases. 3) Insert in our weekly sales newsletter. We have a standing weekly newsletter that the sales enablement team publishes that covers everything the sales team needs to know about in a week. It's ideal to aim for top billing in this newsletter :) This is a subset of the things that we cover for product releases, happy to follow up separately if there are additional questions here. Feel free to reach out on LinkedIn.

This is a great tactic. Research is a great way to drive energy and excitement around a ‘theme’ you want to focus on. I have done this before and it was the single largest pipeline driver for us. We connected the campaign and promotion with another in-person event so that we were streamlining and capitalizing on the momentum we had around that event. The role of sales enablement here was that we used the outcomes of the research to enable the field specifically on discovery and objection handling: 1) Discovery. Good discovery can make or break a deal so building empathy with customers is key, you can use the outcomes of the research to ask comparative questions of prospects and open a dialogue around these key areas. 2) Objection handling. Focus on the data and insights from the HBR work that you can align to your differentiating features or benefits.

This is a great question too. Competitive is one part of the “swiss army knife” of skills a product marketer needs in their skill belt (others being, storytelling/narrative building, relationship building, public speaking, data analysis, etc). My approach is that every product marketer needs to have a pulse on what is happening in their competitive environment. At Twilio, we currently don't have dedicated resources for competitive so we started at the macro-level and worked our way down. 1) Competitive landscape. How is your company/product positioned vs the competitor? Build a high level presentation that shows your key differentiators vs your key competitors in your market. If you have a defined set of market segments, then also make sure you cover differentiation by segment. 2) Objection handling and FUD against top competitors. You should know who the main competitors you face are and it's likely that there are some specific questions that you can focus on to both educate your sales team on how to handle objections as well as get your prospects/customers to focus on what matters and why your solution is more favorable. 3) Ad-hoc requests. Things come up like new product announcements and acquisitions and you need to act a bit like a journalist writing your hot take when these things happen. Quickly document your thoughts on the announcement and get some objection handling to your sales team before they ask. If you do, you will be crushing it on your trusted advisor goals! 4) Battlecards. These are awesome if you can carve out the time. If you don't have dedicated resources it can be tough but for major competitors that come up a lot in sales discussions it is likely well worth your time to build a detailed battlecard (including feature comparison matrix) so that your team has a full picture of what you do vs the competitor. 5) For extra credit - a point person. We had a product marketer put up their hand to say they really like competitive and they wanted to build their skills with cross functional projects. This person took on the competitive role internally, and they send out a monthly competitive overview to the sales team.

The ultimate goal of sales enablement is to make sure the sales team is equipped to sell but also, they should “sell what's on the truck.” You can use the same mental model to justify the amount of sales enablement as you do when prioritizing: 1) Where are the biggest areas of opportunity? Are there any specific products or use cases where we are differentiated and we have a clear runway of opportunity? We should prioritize our efforts here. 2) Are there some products that are just ‘easier’ to sell? We should give our sales team the opportunity to get some quick wins in. They run on a commission basis so make them happy by giving them some 'easy to close' opportunities out of the gate. 3) Are there emerging product areas, or a market that your company wants to break into and you need to generate energy and excitement around? If yes, then this should also be an element you consider.

I encourage my team to be the ‘mini CMO’ for the products they cover. That means the single biggest metric to measure is pipeline (with a focus on pipeline generation). Depending on the specific in-quarter activities we have going on around sales enablement, we can see a dedicated focus on sales enablement and education show up in our sales-sourced pipeline in the trailing quarter. My advice here is to track a few things: Attributed pipeline = how are all your content activities showing up in your pipeline efforts, eBooks, webinars, etc. Sales-Sourced Pipeline = Did you focus on a specific and deliberate effort around sales enablement that you can tie to an increase in sales sourced pipeline around a specific product or use case?

Prioritization is always tough. Every stakeholder has a different perspective on what they are looking to achieve. The ultimate goal of sales enablement is to make sure the sales team is equipped to sell and i’d also add they should focus on “selling what is on the truck.” To share a bit more of my mental model about the elements to consider when prioritizing: 1) Where are the biggest areas of opportunity? Are there any specific products or use cases where we are differentiated and we have a clear runway of opportunity? We should prioritize our efforts here. 2) Are there some products that are just ‘easier’ to sell? We should give our sales team the opportunity to get some quick wins in. They run on a commission basis so make them happy by giving them some easy to get opportunities closed out of the gate. 3) Are there emerging product areas, or a market that your company wants to break into and you need to generate energy and excitement around? If yes, then this should also be an element you consider. Work with your stakeholders to balance all of these elements and come up with a weighting about where you want to direct your sales team. What falls out of this is a prioritized list of product areas to focus your energy around.