Charles Tsang

Charles TsangShare

Head of Marketing, Pinwheel
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Charles Tsang
Charles Tsang
Head of Marketing, PinwheelFebruary 9

This is likely something that can differ a bit depending on company and organization, but in general:

  • Sales Ops functions are focused on strategies, systems, and processes related to stuff like sales forecasting, quota assignment, sales comp design, sales coverage, and administration/maintainance of a company's CRM and lead management systems. All this is of course done in service to not only enable sales, but also execute on the desired sales strategy.  
  • Product Marketing's focus on sales enablement is more oriented around development of content, assets, and sales tools that help a sales rep sell a particular product or solution (e.g., sales decks, demos, case studies).  

In some organizations, there are sales enablement training groups/teams that focus on developing curriculum, courses, and learning design to help upskill sales reps in different selling methodologies (e.g., consultative sales).  

Charles Tsang
Charles Tsang
Head of Marketing, PinwheelFebruary 8

This is a bit of an oversimplification, but I boil down measuring sales enablement success into three categories:

  • Usage: This would be the volume of assets developed as well as ways to measure how often they’re utilized. For example, maybe you post your sales collateral to a sales team portal where downloads / views can be tracked.
  • Quality: This is about getting feedback from sales on how useful the collateral you've developed is, which can be gathered informally in discussions with your sales team or formally through regular internal surveys.  
  • Impact: This would be oriented around correlating the content you develop with metrics such as pipeline influence, win rate, sales rep revenue, etc. This is a mix of art and science though, as it is sometimes not straight forward to be able to tie a particular piece of sales content to a specific business outcome. So think about how to triangulate data points – e.g., did you train a specific group of sales reps in utilizing new sales enablement assets? How do the metrics differ from one group to another?
Charles Tsang
Charles Tsang
Head of Marketing, PinwheelFebruary 9

In one of the earlier questions I was asked about how often I meet with the sales team. In general I meet with them at a minimum once a week, but most of the time several times a week.  

What I like to do during these sessions is to:

  • Begin to understand their needs and where they need the most help. For example, as they work on engaging with prospects, are there common sticking points that come up in sales conversations (e.g., pricing, competitive differentiation)? What are those sticking points and why are they occuring?
  • Share a point of view or strawman. Blank sheet discussions to collect input are helpful, but should be rapidly translated into a strawman proposal or framework for input. Engaging with sales for input is sometimes easier if they have something to react to.  
  • Then, review draft content and solicit their input in stress testing it and poking holes at it. Since sales is on the front lines, they usually have great insight into potential areas where a product pitch or message may not resonate.  
  • Lastly, another interesting way to engage with Sales on this is to get feedback on how the sales content resonated during customer conversations (or better yet, shadow them during a call with a potential customer!)  
Charles Tsang
Charles Tsang
Head of Marketing, PinwheelFebruary 9

It's difficult to paint a broad brush stroke answer on this, but as a general rule of thumb:

  • Meet with Sales to understand their expectations and where they need the most help. It all starts with a conversation to understand gaps/opportunities.  
  • In most cases, Sales will look to Product Marketers to help ensure they have impactful content/assets (informed by research/insights) to help them sell. I have not met many sales reps that are interested (or have the time) to develop sales content on their own.  
  • That said, you should set the expectation that input from the Sales team will be crucial to ensure you're successful. They're on the front lines of talking with prospects, so they have unique on-the-ground insight on common customer questions, sticking points, etc. So they should expect that you'll meet with them regularly to collect their feedback on draft collateral as well as hear about how well some of the sales enablement assets are performing.  
    • On a related point, oftentimes in order to develop things like customer case studies/testimonials, you'll need direct involve from Sales. While they may not be creating the content, they can help you prioritize and identify potential customers to focus on, etc.  
Charles Tsang
Charles Tsang
Head of Marketing, PinwheelFebruary 8

Fintech is definitely a dynamic and ever evolving space – which makes it super exciting! What’s interesting about Visa’s role here is that we sit at the center as a network and have exposure to and partner with fintechs of various shapes and sizes. So speaking a common language is less of an issue at Visa given our extensive engagement in fintech (we like to think of ourselves as the world’s first fintech).

That said, this is a super valid question. Standard messaging documents that sales reps can utilize to ensure there is a common talk track are beneficial. These sometimes operate as standalone documents or could be anchored with a product/solution pitch deck (as a part of the speaker notes).

What I’ve also seen work well, especially when it comes to ensuring sales reps have a common understanding of relevant industry dynamics, is to create an internal education content series. For example, when I was working at Hewlett Packard Enterprise, our Sales Enablement teams did a phenomenal job of creating internal training content on different industry trends impacting our customers – e.g., Cloud Transformation, Big Data. These helped to get reps educated on the latest industry trends and also how to talk to customers about these topics.

Charles Tsang
Charles Tsang
Head of Marketing, PinwheelFebruary 8
  • The answer depends a bit on the situation. Here are two scenarios/examples. 
    • Scenario 1: Sometimes sales has a ton of institutional knowledge around their target customers. This might be because of the history they’ve had around this sales motion/target audience and how long the company has been focused on selling a particular type of product or solution. Using a Visa example, our sales team has had years of experience working on selling our core products to heads of card programs at financial institutions. In this scenario, customer personas may not be super beneficial to Sales (although they can be very beneficial to Marketing, in order to develop great creative/content)!  
    • Scenario 2: If you’re working at a company that is focused on engaging with a new audience or new types of buyers, in these cases there is not a lot of institutional knowledge or insight into who these buyers are. Using another Visa example, over the past few years we’ve been developing new products that target new verticals (to us) – such as insurance companies. In these instances, customer personas can be invaluable for Sales!
Charles Tsang
Charles Tsang
Head of Marketing, PinwheelFebruary 9

A lot I could go into here, but I'd oversimplify the steps into a few areas:

  1.  Sales strategy and sales model: Start with understanding how this works at your company. How is sales structured - e.g., is it all direct sales, or a mix of direct and indirect? What is the sales coverage strategy - e.g., generalists vs. generalists + specialists? Inside sales vs. outside sales? Do you have named account coverage or do the reps cover territories? These factors play a big role how you'd structure your sales enablement strategy.  
  2.  Messaging and content: Based on the above + your understanding of the target customers, insights you have around them, and the products/solutions that your company provides - think about developing buyer/solution/product messaging that can resonate and create it! A great thing to do is to get feedback from sales on this as they'll understand what are common customer objections that the messaging should pre-empt. I like to do this during my meetings with the sales teams (or even better, during customer calls where you can be a fly on the wall).  
  3.  Training, technology, and measurement: If sales enablement is new to the company, it's likely there isn't a protocol around this. Consider the basics from content repositories to store sales tools all the way to training/coaching programs to help upskill sales reps. Lastly, start thinking about reporting processes and technology enabled solutions to measure your sales enablement efforts. Three simple buckets of measurement are (a) Usage (usage of tools), (b) Quality (sales rep feedback), and (c) Impact (correlation to biz results, deal closure, revenue).  
Charles Tsang
Charles Tsang
Head of Marketing, PinwheelFebruary 8

This is particularly relevant to Visa given our global nature and the 200+ countries we operate in. The biggest challenge I encounter is how unique each country / market is, and by extension how that influences the customer mindset and how sales should engage with them.

That said, although different customers in different countries may think about things in different ways, there are always common denominators. Most companies with global sales teams have some notion of regional hubs or regional HQs.  

Lean on your regional counterparts / leads to better understand and align on what these common denominators are – and design your sales support model and content you develop to service what is common vs. what is completely unique to a given market.

Charles Tsang
Charles Tsang
Head of Marketing, PinwheelFebruary 8

In my experience it’s a healthy mix. A few key factors (not exhaustive) can should influence the type (and volume) of sales enablement content you deliver in a quarter:

  • Stage of product lifecycle: How mature is the product and where is it in its lifecycle? This usually will dictate the volume and fidelity of the content you produce. For example, for early stage products, it’s best to keep sales enablement content light as you’re still in the process of assessing early customer feedback
  • Sales feedback: Discuss what tools and assets will be most beneficial to facilitating customer conversations (especially if sales has had a chance to engage prospects / leads already). Are there priority sticking points that need to be resolved (e.g., why your solution vs. competitor X, etc.)
  • Resourcing: Let’s face it - budgets and hours in the day are not unlimited. Be realistic about what type of content capacity you have at your disposal. Based on these constraints, prioritize around the assets that will drive the greatest impact.
Charles Tsang
Charles Tsang
Head of Marketing, PinwheelFebruary 8

For me personally I meet with the sales team at a minimum on a weekly basis. This is usually time well spent as I get visibility into the deals they are working and where there may or may not be roadblocks. It also gives me an opportunity to discuss content, enablement, and GTM plans with the team.  


That said, I would say that during most weeks, in addition to these weekly meetings, I meet or have ad-hoc discussions with the sales team several times over the course of the week.  

Credentials & Highlights
Head of Marketing at Pinwheel
Product Marketing AMA Contributor
Lives In San Jose, California
Knows About Building a Product Marketing Team, Sales Enablement, Stakeholder Management