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Straight From the Stage: Overcome B2B Sales Challenges with Ian Adams


At Yesware, we talk to customers every day. It is the single most important activity for us to understand their current challenges and identify ways for us to help as a company.

An example of this is through our #1 Challenge Survey. A lot of our blog subscribers are current customers, but also future customers. Right now, we have a survey that goes out to everyone who subscribes to our blog newsletter. In this survey, we ask the question “What is your #1 biggest sales challenge right now?” For this Q&A, we thought it made sense to use direct responses from this survey that are most relevant to the current times. For each of these questions, we’ve written blogs on as well, which I’ll link to below.


Q: I’m having trouble breaking into net new businesses via prospecting emails. How do you really engage and connect with prospects via cold outreach?

We have regular conversations with sales reps whose inbound leads are drying up, putting them in a position where they need to reignite their cold emailing/cold calling strategy. Reps are having to quickly develop an inside sales outbound prospecting motion to fill their pipeline with new opportunities.

For prospecting emails, a crucial factor is providing value to the recipient (i.e. providing them with a guide or relevant studies, introducing a business connection, inviting them to a virtual conference or virtual event, providing a research brief, etc). Warm your cold leads up - compliment them, address them specifically, relate to them, be personable, and talk like a human.

Another key element I think every sales rep should be doing is testing new things. With the rapidly changing sales space, techniques and strategies are increasingly changing. Be unique and test different subject lines and phrases. A/B test your templates and see for yourself what messaging is getting the most opens and replies. Test different cold call scripts. Test different messaging via social channels like Linkedin. By doing this, you can make data-driven decisions that pertain to your audience. Keep testing, refining, and sharing best practices with your team - you’ll not only refine your message but ultimately have more valuable interactions with customers.

For some more ideas, templates, and tips for cold outreach - check out our blog on reigning cold outreach during these uncertain times.


Q: What are effective ways to identify and qualify leads digitally?

One effective way to do this digitally is through high-level, conversion-focused content. The first step is attracting leads with highly valuable and informative content. You can then move them down the funnel by getting their contact information and from there you have plenty of ways to determine if your product or service would be a good fit.

Another effective tactic is creating highly-focused, bottom-of-the-funnel content - such as product reviews, testimonials, case studies, or competitor comparisons. A prospect who is searching for a tool has most likely researched a few options and have narrowed it down to two or three. So for example, by creating content that compares various tools, you’re going to attract people who are already at the qualification stage in the funnel. They’ve shown their interest in your product by clicking through to your article that’s relevant to their research. For reps, this may sound like you’re depending on marketing to create these assets. That’s not true. Don’t wait around for marketing. We can all take a branded PowerPoint deck and create short pieces of content that are share-worthy with prospects. The quality of the message is more important than the design.

We cover some more ideas in this cheat sheet for B2B sales.

Q: Other than cold outreach, how do I consistently stay top of mind to buyers during these times?

LinkedIn is one of the most effective ways to connect with prospects. After all, you get to qualify them through their work credentials, and they get to determine if you’re the right fit for them all in one place.

One of the first things prospects will see when they land on your profile is your LinkedIn summary. The key is to build a LinkedIn summary with personality that is engaging yet highlights your skills and business in a compelling way. Keep things short, sweet, and to the point. Align your voice and messaging with your prospect’s wants and needs.

On top of your LinkedIn summary, establish thought leadership by sharing content, and engaging with prospects. A great way to show your expertise and build credibility is to share interesting and compelling content. Share industry-related articles, thought-provoking studies, and valuable information. Also, make sure to join social groups and see what industry professionals are talking about, get involved in conversations and you’ll have no problem staying top of mind.

If you want some inspiration for your LinkedIn summary - here are 6 of the best summaries we’ve seen.


Q: Getting so close and then not being able to close the deal. What are some best practices for sales closure?

B2B sellers know that their customers are as informed as ever. But with the vast information at hand, they’re also as overwhelmed as ever. Making a decision isn’t easy, especially buying complex solutions and software. That’s why the best thing you can do as a salesperson is to make it easy for your potential customers.

Some tactics to closing the deal are to offer some urgency or something they’re afraid to miss out on (FOMO is a real thing). Offer a limited-time discount, limited services, or an extra gift or incentive to get them over the hunch. In B2B sales though, you’re much better off building value and understanding the critical event for when they’ll need your offer, rather than giving them a time-sensitive discounted offer. You’ll often miss the deadline and still end up giving them the discount.

Take a look at these 5 insanely effective tactics to get contracts signed this month.



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IAN ADAMS

Ian heads up sales and marketing at Yesware, the easiest to use sales productivity software. Their Gmail / O365 email add-on gives sales professionals everything they need to prospect, schedule meetings, and follow up, right from their inbox. All while giving management the insight into what’s working for their teams to drive revenue growth. With over 1 million installs, customers like Groupon, Yelp, Twitter, and Box use Yesware every day. Ian currently lives outside of Boston with his wife and 2 children. He loves spending time outdoors with family and friends: hiking, surfing, and skiing.


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How Do I Continue to Market and Sell During COVID-19? 

Due to popular demand, we are continuing the Straight From the Stage Q&A Series for the Month of June! 

We spoke with industry thought leaders about how to continue SMART and RESPONSIBLE marketing and sales activities during a pandemic. Topics include B2B sales strategies, inbound marketing, video communications, and more.


Stay tuned for a brand new Q&A every Friday in the month!


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