Episode 246: Jennifer Rizzi on Building an Effective Sales Content Strategy

Sales Enablement PRO Podcast

Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO Podcast. I’m Shawnna Sumaoang. Sales enablement is a constantly evolving space, and we’re here to help professionals stay up to date on the latest trends and best practices so that they can be more effective in their jobs.

Today I’m excited to have Jennifer Rizzi from Squarespace join us. Jennifer, I would love for you to introduce yourself, your role, and your organization to our audience.

Jennifer Rizzi: Thank you so much for having me, Shawnna. My name is Jennifer Rizzi and I am the sales enablement manager for the enterprise team at Squarespace. My background is actually in journalism, believe it or not, and my career took several interesting turns to end up in my current role supporting technology sales, but I love it and I wouldn’t have it any other way.

I started off in TV reporting and I worked as an on-air reporter in two state capitals, Harrisburg, Pennsylvania, and Charleston, West Virginia. After that, I relocated to New York City and I became the first iPhone-only video reporter for the New York Daily News, and I used a storytelling app called Videolicious, which was very revolutionary for the time. Not many people were using iPhones to report, and my content there really helped the sales process for that company.

Videolicious was acquired by Squarespace in 2019, and that’s where I moved into my current role, which really blends my passion for content creation with my experience selling. I support the sales of our B2B enterprise product, which is a version of our website builder that’s made to serve complex organizations. Now, you might be familiar with Squarespace as a leader in website design for individuals and small businesses, but we also do support major companies with enterprise-grade security and team collaboration features.

SS: We’re excited to have you here, Jennifer, and what an interesting story about how you’ve ended up in the enablement space. I love learning more about your background. Now, I’d love to also understand from your perspective, at a high level, how would you say that enterprise-level sales enablement differs from sales enablement focused on other market segments.

JR: That’s a great question. I would say that I think enterprise companies have different needs and expectations throughout the sales process and rarely do enterprise buyers make decisions alone. They’re usually part of a decision-making team, or they’re an influencer at their organization who can persuade supervisors or colleagues to adopt their recommendations.

The content that you equip your sales teams with should be very shareable. It should be succinct and pithy, and it really should convey your value prop instantly to anyone who comes across it. Even if they don’t know your product and they weren’t part of previous sales conversations, it should be able to stand alone and convince audiences of your product’s value at first glance, even if they have no background.

SS: I love that. I also have some experience with enterprise deals and they are notorious for having long sales cycles. How can enablement help reps to accelerate those sales cycles?

JR: I think it’s really about qualifying prospects as much as possible before they have that discovery call or before they meet with an AE for the first time. Ideally, you want your prospects to self-select based on the content you publish online. You want them to get really excited after reading a blog or a white paper that speaks to their needs and then raise their hand for a meeting. In a perfect world, of course, it doesn’t always work that way, but you want to strive for that.

Then throughout the sales funnel, you want to keep providing prospects with relevant content that’s tailored to their particular needs and concerns, and that preemptively addresses them. That way you’ll have educated prospects who join your sales meetings and you’ll save really valuable time going over ideas that a piece of content could have communicated to them beforehand.

SS: Absolutely. You talked about the interesting dynamic within enterprise deals around having multiple people as part of the buying decision. With a lot of enterprise buyers, relationship building is absolutely key between the rep and not only the key buyer but actually multiple buyers within the organization. How do you equip reps to effectively engage buyers in a multi-threaded way throughout the sales process?

JR: As I touched on just a little bit earlier, you really want your reps to be skilled at adding value to buyers’ professional workflows, and you want them to essentially perform a consultative role in their sales discussions showing that you understand the issues they face and the goals that your prospects need to meet and that you have the right knowledge to help them navigate those. That’s what’s going to build those relationship bridges.

You want to position yourself as a resource they can count on to be in their corner who has their best interest in mind. That way you’re going to stay top of mind when they need that solution and they’re going to feel really comfortable coming to you.

SS: I love that. Now I do want to shift gears a little bit because you mentioned on LinkedIn that one of your areas of expertise is creating content to help reps guide their buyers, kind of like you just mentioned through the sales funnel. In your opinion, what are some of the key components of an effective sales content strategy?

JR: I think listening to your sales team and gathering their input is so important for producing content that really resonates with prospects. They’re the ones in the trenches having those conversations every day, whether it’s over email or over sales calls, they’re seeing what prospects respond to and where they get stuck in the funnel. Lean on their perspective to really diagnose what content will help prospects get unstuck, and what common questions can be answered more efficiently with content saving time on those sales calls.

I really believe that reps should view sales enablement as a partner working with them in strategy, and they should always feel comfortable bringing ideas to you with the confidence that they’re going to be heard and validated. It’s really important that they feel that validation. Even if you can’t deliver exactly what they’re asking for at a given time, maybe you don’t have the bandwidth or the resources, you can still use your content expertise to suggest an alternative path that may be a more efficient way to get their message across and accomplish the same goal.

SS: Now you also mentioned the importance of using customer-centric language, especially when you’re positioning enterprise products. Why is customer centricity so important, especially in times of economic uncertainty like we’re experiencing today?

JR: I really love this question and I think as Donald Miller put it so eloquently in his book, Building a Brand Story, your customers need to feel like they’re the hero in the sales journey. Too often sales reps make the mistake, I think, of trying to swoop in unsolicited to just be a customer’s white knight with the solution to all of their problems, when in reality that customer might not feel that they need to be rescued and they might even be resistant to that idea out of pride or for other reasons.

When you flip the script and you position them as the hero and you put yourself in the role of the mentor or guide, or the knowledgeable one that helps them achieve their full potential, that’s when they’re going to be open to building a relationship and partnering with you.

SS: I love that. How do you infuse that same notion of customer centricity into your sales content strategy?

JR: I think being mindful of your customer’s time is key. In enterprise sales your prospects are all busy professionals with a lot on their plate, so you can’t really expect them to devote a ton of time to consuming your content in the way you want them to necessarily, or also to engaging in quirky, novel experiences the way the general public might respond to.

Sometimes simple formats, just like a one-sheet, slide decks, and landing pages are the most effective at getting your message out, and you really want to be direct with your message and elegant. Speak to customers like the educated professionals they are. Avoid being overly casual and using slang unless your brand voice is known for that and just keep your content short and easily digestible.

I’m a big fan of using video whenever possible because it’s a really visual, engaging medium and links are very shareable. Video is something that viewers can possibly consume without much effort, so you really want to try and lower that effort bar as much as possible to consume your content.

SS: I love that advice. Last question for you, Jennifer. What advice would you give to other enablement practitioners to help get their reps to better engage buyers through content?

JR: I would say just try different types of content. Keep iterating based on learnings. Be open to ideas from your team and be really prolific with your content creation. Try to be agile in supporting sales rep needs. We know they can always change based on your product offerings and just larger economic patterns, so be reactive to that, be mindful of that, and just really try to adapt your tone to your audience and learn what they care about. Then deliver what they need before they even ask for it.

SS: I think that’s fantastic advice. Jennifer, thank you so much for joining us. I really appreciate your time and your insights.

JR: Absolutely. Thank you again for having me. Really enjoyed it.

SS: To our audience, thanks for listening. For more insights, tips, and expertise from sales enablement leaders, visit salesenablement.pro. If there is something you’d like to share or a topic you’d like to learn more about, please let us know we’d love to hear from you.