Episode 432Sales EnablementContent StrategyRevenue Operations

Don't Be Afraid to Create Less with Jessika Ward

Jessika Ward, a 13-year sales enablement veteran who has built programs from scratch at multiple SaaS startups, argues that the biggest shift enablement teams can make is redefining their function — from content and training generation to performance management. She explains why seller attention is a commodity that should be protected at all costs, and why the best enablement content feels like a shortcut, not homework — showing up when sellers are stuck rather than waiting for a calendar event. Jessika introduces an 'air traffic control' model for enablement where one curated signal per week replaces the noise of competing teams fighting for seller attention. She also challenges the industry's reliance on engagement and course-completion metrics, arguing that observable behavior change and revenue outcomes — deal velocity, pipeline generated, time to close — are the only metrics that matter. Her closing advice: start with the business problem, respect seller attention, and don't be afraid to create less.

Jessika Ward

Jessika Ward

Sales Enablement Leader | 13 Years in SaaS

15 min

Key Takeaways

  • 1Enablement should be redefined as a performance management function, not a content or training generation function — the goal is behavior change that influences performance, not knowledge transfer
  • 2Seller attention is a commodity that should be protected at all costs — every minute spent on enablement content is a minute away from selling, so content must earn its place
  • 3The best enablement content feels like a shortcut, not homework — it finds sellers when they're already stuck and helps them move forward immediately, rather than waiting for a scheduled training event
  • 4Use an 'air traffic control' model: be the single filter for all the messages competing for seller attention from marketing, product, management, and methodology teams — one curated signal per week beats a flood of noise
  • 5Stop measuring enablement by engagement metrics and course completion — measure observable behavior change and revenue outcomes like deal velocity, pipeline generated, and whether sellers actually did something differently

About this episode

Enablement teams are drowning in content requests, but Jessika Ward says the answer isn't producing more — it's producing less and making it count. With 13 years of building enablement programs from scratch at SaaS startups, Jessika has learned that seller attention is a commodity, and the best content shows up when reps are stuck, not when a training calendar says so. In this episode, she breaks down her 'air traffic control' approach to filtering noise, why engagement metrics are vanity metrics for enablement, and how to measure what actually matters: did a seller do something differently?

Topics covered

  • Enablement as performance management vs. content generation
  • Protecting seller attention as a scarce commodity
  • Meeting sellers where they are in their workflow
  • The air traffic control model for enablement communication
  • Behavior-based metrics vs. engagement vanity metrics

Notable quotes

Any attention that you're taking away from the seller is time that they're spending away from selling.

Jessika Ward(6:48)

Enablement content should feel like a shortcut, not homework. And it should find them when they're already stuck.

Jessika Ward(7:50)

Engagement tells me if something was seen, but the behavior will tell me if it mattered.

Jessika Ward(12:06)

Start with the business problem, respect seller attention, and don't be afraid to create less.

Jessika Ward(13:34)

Resources mentioned

  • Framework

    Air Traffic Control Model for Enablement

    Position enablement as the single filter for all messages competing for seller attention — from marketing, product, management, and methodology teams. Curate one high-signal post or roundup per week. If content doesn't directly connect to a target behavior or revenue metric (deal velocity, pipeline, stalled deals), it doesn't belong. This builds trust with sellers who learn that when enablement speaks, it's worth listening.

  • Framework

    Behavior-First Content Prioritization

    Instead of responding to every content request, start with the observable behaviors you want to drive — did sellers reach out sooner? Did deal strategy change? Did stalled deals move? Work backward from revenue outcomes to determine what content to create, and use data from top performers to identify which behaviors actually correlate with results. If a piece of content doesn't map to a specific behavior change, deprioritize it.

  • Framework

    Meeting Sellers in Their Workflow

    Shadow sellers to understand their actual day-to-day tools and flow. Map where they get stuck and where content could serve as an in-the-moment shortcut. Place enablement content inside the tools they're already using rather than requiring them to go to a separate platform. If sellers have to pause their day to consume content, it's too heavy and probably too late.

Benjamin Ard (00:55) welcome back to another episode of Content to Close. Today I'm joined by Jessica. Jessica, welcome to the show. Jessika Ward (01:01) Thank you. Thank you for having me. Benjamin Ard (01:03) Yeah, Jessica, I'm excited for today's conversation. I think it's going to be a fun one. think a lot of people need to hear some of these messages we're going to talk about in the subject. But before we dive in, Jessica, let's get to know you. Tell us about yourself, your background, work history, all that kind of fun stuff. That way we kind of get to know you before the audience hears a little bit more about sales enablement. Jessika Ward (01:24) Perfect. I'm Jessica. I've been in enablement for 13 years now. I have mostly been in SaaS startups. So being the first enablement person hire at a company is in building enablement programs from the ground up. I've been in small companies as small as 45 people to larger companies as big as 1,000 and more. all focused on revenue generating, go-to-market motions and strategy, and anything from small SMB sales cycles to large enterprise, multi-million, multi-year contracts. Benjamin Ard (02:04) I love it. That's amazing. Incredible background. Someone with 13 years of enablement experience for an area that kind of is just really kind of hitting a peak and kind of starting to get some momentum is a rarity. So I'm excited to have your expertise on the show. This is going to be a ton of fun. So for everyone listening, what we're going to talk about is operational content strategy. And basically what that means is how we organize and manage content. So it actually drives revenue. Those are the magic words. So Jessica, to set the stage, how do you define useful content when the goal is supporting sales? What does that look like for you? Jessika Ward (02:44) Yeah. So I think the first shift for me is the definition of enablement, utilizing the function as a performance management function and not content or training generation. And so when I think about organizing content that actually moves revenue or creating content that is revenue generating, it's all about the behavior changes that we want to see. that will actually influence performance. A lot of times we focus on content that's knowledge and we're not actually focused on the things that are going to help a seller take action in that moment that's gonna actually move the needle. Benjamin Ard (03:26) I love that. Okay. So it's in the process is performance based. It's helping individuals actually improve and perfect themselves and get better. Now with artificial intelligence, I'm throwing that out way too early in an episode, but it's out there. Can't take it back. There's this struggle with quantity and quality and like knowing what to make, how much of it to make the cadence. When something should be refreshed or created from new, how do you kind of determine the priorities and when and what and how much of it that you're working on? Jessika Ward (04:01) Yeah, so this is a great question because you mentioned it. I have found that the requests for content is never ending. And if you only focus on the subjects, how many case studies you can produce, how many different modalities, some people want short form content that's in a video, some people want one pagers, some people want... like actual courses, everybody has their different idea of what they think is going to be the game changer when it comes to content. And I think really enablement professionals need to get more comfortable with not creating content. You know, I think we the instinct is to train or the instinct is to throw material at them in order to prove that enablement is busy or that we're useful or that we're valuable based on the amount of content that we create. And so I think the biggest shifts for me were changing the timing and the visibility of the information and found that that had a bigger impact than, you know, any course that we could create or any one pager this week or, you know, just really getting vigilant on prioritization of looking at the behaviors that we were trying to drive, right? And which ones were having the biggest impact. So looking at the things that we're working for the sellers that are top performers and maybe where there were other opportunities and using data and insights to drive like, okay, if I'm looking at funnel, for example, know, deals are stalling and using those decisions, that information to drive your content generation and your, you know, your training. really don't love that word, but you're training materials, your enablement programs around those things rather than just like the volume and where content lives and how often you're putting it in front of people. Benjamin Ard (05:57) I love it. And I love how it's rooted in data. You're finding the insights to figure out what should actually be there. You're looking in the CRM, you're looking at the data. I love everything about that. So when it comes to content adoption, sometimes it's a little rough. People in general were creatures of habit. And when you get into a groove, sometimes it's hard to break that groove and introduce something new into the mix. What are you finding from that perspective of introducing new content when you've maybe edited or created a new version of content? Where are you putting it? How are you influencing change? I'm going to avoid the words training here, but what are you doing to help the adoption just across the board and really prove the value of maybe taking a different approach and really taking advantage of this new content and materials. Jessika Ward (06:48) Yeah, it's a great question. Lots of layers in there. So I think the first thing that I'll mention is like a seller's attention is a commodity and it's something that should be protected at all costs. I always say like any attention that you're taking away from the seller is time that they're spending away from selling. And so there's a couple of ways to both protect them but also as an enablement professional trying to drive impact and influence performance and behavior. I think we have to think about how sellers actually experience content and where they are in their day to day. So if you're just getting started and you're trying to figure out, what content is actually going to help sellers? One, ask them. Two is shadow them and see what tools they're in, what their flow is for how they're moving through different applications, things like that. That will usually give me a clue from like where in their day to day it makes sense for content to live and meet them where they already are. So enablement content should feel like a shortcut, not homework. And it should find them when they're already stuck. I feel like if they have to pause their day or or whatever they're in and they have to sit down and consume it, it's too heavy and it's probably too late. So I think the best content shows up when they're stuck and helps them move forward immediately or the timing, you're not waiting for a calendar event for enablement to get to that. Benjamin Ard (08:23) Okay. I really love that. the whole part about it's when they're stuck, like content can help me get out of a groove, help me figure out what to do when I'm not quite sure what to do next. Let me turn to the content. This is an additional resource that's there to help me instead of a burden that's meant to get in my way, take up my time, things like that. When I do have a momentum. things of that nature. So I love that it's kind of that life preserver that can kind of help them move forward and get out of the mud, kind of an idea. Jessika Ward (08:48) Yeah. We love analogies. We call it air traffic control, right? Think about all of the different teams that are trying to get a seller's attention. You have marketing that wants their attention. They've got to get product knowledge out there. They've got their managers who are telling them to use the latest sales methodology, whatever, right? And so I like to think of like, if I was the filter for all of the messages that they were receiving and all they did was pay attention to the one thing that I'm posting that week and you can tell them, hey, Benjamin Ard (08:54) Okay. Jessika Ward (09:18) If you just pay attention to this one post a week or this, you we used to do roundups. It's like, I will, I will protect you and I will filter out all of this stuff that I think is noise. And again, if you've done a really good job of attaching it to the metrics and the behaviors that you're trying to drive, it's really easy to then start whittling things down and being like, does this achieve that particular goal? Do we think it moves? a stalled deal, do we think that it's actually gonna help them get to close faster, increase deal velocity, all the things that we love to hear? If the answer is no, then it's really easy to just be like, then it doesn't belong. Benjamin Ard (10:00) Well, and I'm sure that there was a full process for you to build up the trust with the team to say, I am here to protect your time. I will only show you what is relevant and if it will make an impact, I promise to protect that. I think that's a great enablement gatekeeping role to say, if I say something, You're probably going to want to read it. And I promise if it's not like noteworthy, I'm not going to tell you anything. I'm going to get out of your way. And I think that's super cool. Jessika Ward (10:27) Absolutely. Enable my earns trust when sellers feel understood. They're not here to be educated. I think a lot of enablement professionals are like, I'm certified in all of these different sales methodologies. And I know all of the market research and intelligence and things like that. And I'm here to teach you something. And I think that if we shifted that to think about I am here to make your life easier. And the best way that I can do it is understand what your everyday looks like and what customers are saying to you and what's actually happening that will earn you that, that spot at the table where they start coming to you with ideas and start actually treating you like more of an advisor and a consultant than, than a professor. Benjamin Ard (11:14) I it. I love it. That's cool. And I like the definition of the role. You know, it's not preaching to a group of people. It is an advisor. You talked about metrics and things that kind of prove that it's actually worth their time. What are the golden metrics for you? What do you look at to know that content's doing the trick? Because that informs so many decisions. Does it need to be replaced? Should it be promoted? Should it actually get on people's radar? What are you looking at specifically to kind of know the performance of content? Jessika Ward (11:46) I love this because again, I think that maybe this is a challenging, another challenging idea because I think a lot of times we default to engagement metrics. Are they looking at it? Are they consuming it? Do they like it? I feel like, again, going back to being a performance consultant, start with observable behavior. Start with the things of... Did a seller do something differently? Did they reach out sooner? Did the deal strategy change? Engagement tells me if something was seen, but the behavior will tell me if it mattered. And I think that as far as what behaviors you're looking at, go back to revenue outcomes. mean, that deal velocity, pipeline generated, all of the things that matter to a revenue organization. Those should be the metrics that are driving your enablement engine, not course completion or knowledge, getting an 80 % pass on their ability to short-term recall the quiz information on the 10-minute video they just watched. Benjamin Ard (12:54) So you're getting rid of the whole vanity metrics, the engagement, all that kind of stuff and going straight to the disimpact revenue. I love that. Okay, one final question, because we're running out of time and we keep these episodes short because enablement leaders are busy. For a business who's listening to this, any enablement leader who's like, yeah, we need help here. I need to figure out something to do. We need to improve here. What would you recommend they do today that they can start working on to better organize, better increase adoption, better track, anything that you've talked about today, any recommendations, like if you were sitting in their chair, what they should do today to kind of get the motion going. Jessika Ward (13:34) start with the business problem, respect seller attention, and don't be afraid to create less. Benjamin Ard (13:40) love it. That's very cool. Don't be afraid to create less. That is a quote that I literally just marked because I love it. I think that's going to be a great title for this. Jessika Ward (13:50) Yeah, we try to be everywhere but nowhere. And I think that again, our lists of requests can grow until we're overwhelmed and then we're paralyzed because we don't know where to start. Benjamin Ard (14:01) Yeah, I love that. Well, Jessica, thank you so much for your time and insights today. It has been absolutely amazing. For anyone listening that wants to reach out and connect with you online, how and where can they find you? Jessika Ward (14:12) Great question. I am on LinkedIn. That's where you can find me. Benjamin Ard (14:17) Love it. Anyone listening, scroll down to the show notes, regardless of what platform you're on, we will link to Jessica's LinkedIn profile right there. Click on her name, connect with her on LinkedIn, say hi, say you're from the podcast, add someone amazing to your network. think it'll be great. Jessica, again, thank you, thank you, thank you. I really do appreciate the time and insights today. Jessika Ward (14:36) Again, thank you for having me. It was a pleasure.

About the guest

Jessika Ward

Jessika Ward

Sales Enablement Leader | 13 Years in SaaS

Jessika Ward is a sales enablement leader with 13 years of experience building enablement programs from the ground up at SaaS startups. She has been the first enablement hire at multiple companies, working across organizations ranging from 45 to over 1,000 employees. Her experience spans the full spectrum of go-to-market motions — from small SMB sales cycles to large enterprise, multi-million, multi-year contracts. Jessika approaches enablement as a performance management function, not a content or training factory, and is known for protecting seller attention while driving measurable revenue impact.

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Frequently Asked Questions

Jessika recommends starting with the business problem and working backward from revenue outcomes. Instead of responding to every request for case studies, one-pagers, or courses, identify the specific behaviors you're trying to drive — like reaching out sooner, changing deal strategy, or moving stalled deals. If a content request doesn't map to an observable behavior change tied to revenue, deprioritize it. This requires getting comfortable with saying no and creating less.

Jessika argues for measuring observable behavior change and revenue outcomes — deal velocity, pipeline generated, whether sellers actually did something differently after consuming content. Engagement metrics (views, completion rates, quiz scores) only tell you if something was seen, not if it mattered. The shift is from 'did they learn it?' to 'did they do something different because of it?'

Enablement earns trust when sellers feel understood, not educated. Instead of approaching sellers as a teacher with certifications and methodology expertise, approach them as someone who understands their everyday reality — what customers are saying, what's actually happening in deals, what tools they use. Shadow them, ask them directly, and position yourself as an advisor who makes their life easier, not a professor who assigns homework.

Every minute a seller spends on enablement content is a minute away from selling. Jessika recommends acting as an 'air traffic controller' — filtering the flood of messages from marketing, product, and management into one curated weekly signal. Content should find sellers when they're already stuck in their workflow, not require them to stop what they're doing. If they have to pause their day to consume it, it's too heavy.

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