AMA: Upwork Former Head of Product Marketing, Anjali Cameron on Go-to-Market Messaging

Similar to the question above on uncovering buyer trends, I’d suggest starting broad and then going narrow to develop market driven messaging. Start with a few key insights about your target market and their pain points. I leverage personas for this. If you don’t have them, the work should start there to really understand your customer’s needs and concerns. From there, I would build some options and do high-level testing with focus groups or customer panels. I’ve also done this via quantitative surveys where you ask prospects to react and rate how they resonate to different messages. You can also always test in market if you have the capability. For instance a demand test to run ads with message x and measure performance against your usual slate of market messages. If it fairs well, you can go a level deeper and create a test landing page experience to see how well the messaging converts.

I’d focus mainly on all the things you can do to stand out: 1. Make your visual layout, pricing and customer experience unique to further differentiate your offering from competitors. The messaging is the wrapper for all of this but these pieces can really help you speak to your unique value prop. 2. Talk to your customers that have used your competitors and find out where you are truly differentiated and then hammer that home in the messaging. 3. Give customers a reason to try you versus the competition. Free trials, better customer service, whatever it takes to stand out. If all else fails, or when they take it too far, I know legal action can be taken if a competitor is blatantly scraping your site and creating a replica.

Be clear on your target and start there. If you’re a marketplace, force primary and secondary segments. And if you’ve got multiple business lines and segments with unique pain points, align on a clear hierarchy and where in your funnel you can speak to different audiences. I’d say the fewer segments the better. It leads to less confusion internally and externally. As you do research on your segmentation, in addition to unique needs and pain points, look for commonalities. That will help ensure that you have overarching messaging that resonates with most and then you can tailor that core message per segment.

Agreed that often in the race to get a product to market, teams will put their best messaging idea forth, run it out for a quick test and then launch. I think there are a few ways to check that you’re on the right path or if pausing is required. 1. Internal comprehension - at least in the case of Upwork we’re lucky that we collaborate with many freelancers internally. So when they see the messaging and find it confusing or have a lot of questions about a launch that are clearly not obvious through the product or available messaging, that’s a good time to pause. So use your internal folks to give you a read on potential issues with the messaging. 2. Target audience comprehension - when you launch, you may hear feedback from your most vocal sales reps and the loudest voices in a community forum. That said, these may not be your target audience. If however, you hear negative or confused feedback from the very people you designed the messaging for, it’s time to pause and circle back with this audience to understand what’s going on and how you can bring more clarity. 3. Unintended audience comprehension - a nuance to the point above is that you may have customers outside of your target for whom this feature isn’t valuable but due to messaging confusion you feel are at risk for churn or reduced engagement. In that case, pausing and refining your messaging for these secondary audiences can be important.

Great question and not an easy one. There’s a difference between saying, “let’s shift messaging to go upmarket but retain and continue to build for our core SMB base” versus “let’s shift messaging and resources to go all in on upmarket, even if that means neglecting SMB.” If it’s the former, it’s much easier to do because you can shift all your prospect messaging upmarket but continue to engage and speak to your SMB base as you have been. And you’ll still have a product ladder or offerings that meet the needs of your SMB and so you can effectively segment and tailor messaging. For example, SMB ads can go to SMB landing experiences and upmarket targets can have their own messaging funnel. If that level of segmentation isn’t possible, and you can only advertise to upmarket, having a visible escape hatch or way to identify SMB is crucial so you can carve those folks off to their own tailored messaging area, even if that is secondary or on a separate page. I’d also focus on ensuring your 100% aligned internally with regards to the conversion expectations of your tailored messaging. If you go fully upmarket in your messaging, are internal stakeholders comfortable losing your SMB conversions? Or is there a threshold you need to maintain in which case you’d want to test your upmarket messaging with SMBs to ensure it’s not too alienating.

For broader buyer trends, I’ve found focus groups with prospects to be effective. It’s a way to get in the heads of prospective buyers and see what’s on their mind. You can get their reaction to several high-level messaging angles and through moderated conversation, you can uncover larger trends versus just buzz. Once you have the key message in place, I’d suggest qualitative research with buyers. I organize these as 1:1 interviews where you share a screen and ask a buyer (prospect or current) to react to written comms. The best way to get a good read is to write comms you’d actually use, so an email for instance, and ask them to read and react. We’ve done this verbally and by using a tool like Zoom where participants can highlight things that make them happy, angry or confused.

This continues to be an evolving process but we leverage a few things: 1. Lead time - sharing the info early so the sales team can disseminate it via the right channels with enough notice (for example, some teams meet just once a week so if you miss that cycle, they may not see it until after launch) 2. Central POC - we have at least one person on sales who has the responsibility of reviewing key messaging and ensuring that updates relevant to sales are flagged via an internal dashboard 3. Visibility - important messaging is delivered and reinforced when possible in sales leadership meetings to ensure that busy sales leaders can take note and flag critical news to their teams

I’m a big believer in experimentation before your messaging hits customers. Typically in the product development and go-to-market planning cycles you have at least two, if not more, opportunities to test different messaging. The first is to sneak it into usability research. If a UI designer is going to run a study on how customers comprehend a product flow, the messaging naturally comes up. When possible, attend the first interview or get detailed notes to see how the customer or prospect is talking about the flow and the words they use to describe it. If the first interviewee doesn’t hit the value prop, give your designer new messaging for the next interview to see if there’s improvement. The second is to run some light messaging research, be that via a customer panel or even a quick couple of calls with some of your target audience. Try different messaging to see what resonates. And typically, yes, what works in one channel can work in others though often with tweaks. In product messaging is typically heavily word count constrained, relying more on the UI and visuals. With email perhaps you have more room. With blogs and collateral even more.

We use a feature messaging brief (or initiative messaging for big projects) to communicate everything from the big picture to the fine details to internal stakeholders. The brief typically contains these sections: Feature description (usually includes screenshots), Target audience, Release and go-to-market plan, Key messaging (2-3 sentence blurb for customers that clearly explains the benefit and if any action is required), Ongoing marketing efforts beyond the GTM, and FAQs. Through some missteps, about a year ago we also started labeling sections with “Internal” and “External” so it’s very clear what can be copy and pasted for customer consumption and what is for internal context only. Given that Upwork has a marketplace and sales arm, we’re also very clear, when we disseminate the brief, about which stakeholders in the company should be educated about this change or feature.