4 Ways to Win Customers with an Always-on Outbound Sales Muscle

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Sellers in B2B tech today are in the eye of a perfect storm. The pandemic-era boom of inbound leads has slowed, but the pressure for sellers to close deals is higher than it’s ever been.

This is a moment for sales teams to rethink their approach to prospecting in an intentional way. A whopping 71% of sellers say they are relying more on outbound sales in 2023 than they did in 2022. The best sales teams will flourish well beyond today’s storm by revisiting the basics and building an always-on, proactive outbound sales motion that is efficient, effective, and personalized.

Here are four ways sales teams can revamp and diversify their outbound playbook to create a sustainable pipeline flow and add new, high-value customer logos to their roster.

Bring new life to the cold call with personalization and an omnichannel approach

Cold calling has been reimagined for the better because of digital media. Social selling, customer referrals, LinkedIn Sales Navigator, text messages, and email plays are some of the most valuable tools your sales team has to break through with prospects. Meet customers where they are with an omnichannel approach, whether that’s online, on the phone, offline, or somewhere in between.

Consider what this could look like: one, use a video recording tool like Loom or Vidyard to record a one minute or less personalized message for your prospect. Two, send that personalized video message to the prospect via LinkedIn Messenger with a call-to-action (CTA) inviting them to reach out to you via email if they’re interested. And three, follow up via text message should the outreach go unacknowledged for a few days.

Approach prospects with confidence, listen, and create an authentic connection by being creative with different channel communications. Encourage your SDRs to let their personalities shine, create a warm environment for initial correspondence, and start building credibility. Personalization translates to more engagement, more meetings, more pipeline.

Educate yourself to earn the right to a conversation

You don’t need to reinvent the wheel to increase deal momentum for your business, but you do need to show up smart to earn the right to a prospect’s time. Whether your CTA is opening an email, booking a meeting, or signing up for a trial, start the relationship off right by educating yourself in advance on your prospect’s role, industry, and the most common challenges others in similar positions are trying to solve.

Once you’ve opened the door to a conversation, it’s about engaging with the buyer and appealing to their business challenges and emotions as a human. Asking the right questions throughout the sales cycle is crucial, but asking them in the beginning is critical: “Why did you agree to take this call with me?” Take the time to ask prospects about their pain points and goals. Why is finding a solution for these pain points a priority now? Which decision-makers will need to be involved from their side? This holistic view will help sellers identify a clear, value-story-based path to closing the deal.

Also ask questions that will help understand what the prospect knows about your product so you can best determine how to address any knowledge gaps. By correcting any missing value propositions, you can ensure your internal champion leaves your first meeting armed with knowledge they can share with decision makers on their side to co-sell on your behalf.

After your first conversation with the prospect, continue discovery. Don’t assume the challenges you discussed in early conversations are the same or the only ones as the evaluation process continues. Validate and revalidate throughout. Then keep trying to help them solve that problem by arming yourself with product messaging, ROI proof points, and relevant customer stories that will appeal to the prospect and help you stay relevant between meetings.

Speed up your outbound approach with AI and automation

Once you’ve tirelessly researched your customers to determine how your product and you can best serve them and you’ve clearly communicated the potential adoption ROI, you’re ready to take the next step together; now it’s time to consider how your sales tech stack can accelerate the deal process.

The average number of interactions for a B2B buying cycle have increased by 54% in 2022. Sellers would be remiss to not leverage collaboration and productivity tools like AI and automation to improve the prospect experience and ensure that time is spent on critical, value-led activities. But the real game-changer with using AI and automation isn’t just that it gives sellers time back by automating tedious tasks like collecting and interpreting data, transcribing sales calls, and initiating email cadences; it’s about what these technologies enable so sellers can be more impactful – to have more authentic interactions with prospects and collaborate better with Customer Experience, Marketing, and Product.

Take the meeting experience. Layering scheduling automation into your sales team’s tech stack is a natural and high-value place to start. Sellers at every level can share their scheduling links in emails and LinkedIn Messenger, making it easy for prospects to book a demo without ever leaving their inbox. With AI tools like Gong Engage sellers can consolidate key enablement touchpoints like prospecting and selling onto a single platform while accessing their meeting availability.

With personalization top of mind, it’s important to keep humanity at the center of the buying experience. Sales leaders and their teams should apply a healthy amount of skepticism with AI and think about where it makes strategic sense and boosts overall team efficiency versus where it creates unnecessary complexity or depersonalizes the buying experience.

Complement outbound with a smart inbound motion

In this day and age, all leads count. To have the most impactful outbound muscle, sales teams need an equally strong inbound muscle to work new business. It goes back to meeting the customer when and where they’re ready to talk to sales. Your cold outreach email could have come at a time when budgets were tight at the prospect’s organization. Thankfully, after an excellent quarter, they’ve reengaged and are ready to learn more about how your product can best serve their needs.

If a prospect is finally ready to click the “Contact Sales” button on your website, your company must be equipped to respond as soon as possible. Solutions like Calendly Routing make this possible – and easy – by helping teams qualify, route, and schedule meetings with high-value leads in real time to help close deals faster. Companies like Smith.ai increased their website conversion rate from marketing-qualified lead to meetings booked by 26% with Routing and drove a 20% increase in sales meetings.

The bottom line impact of outbound sales cannot be overstated. The same study mentioned above found if sellers aren’t doing outbound, they’re leaving up to 50% of potential revenue on the table. No company can afford this. Empower your SDRs to elevate their outbound strategy with memorable, personalized, multi-channel communications; articulate value that shows a deep understanding of the prospect’s goals; and use automation and AI technologies to enrich the experience while keeping the deal moving forward.

Molly McKinstry
Molly McKinstry is the Head of Sales at Calendly. She leads high-performance sales teams to achieve maximum revenue outcomes by showcasing the business value of scheduling automation to the enterprise. Previously, Molly spent over a decade at Glassdoor. She most recently was the Vice President of Global Sales overseeing sales segments across North America and Europe. As a founding member of the sales team, she helped establish Glassdoor’s go-to-market motion, including scaling from a 10-person sales team to over 300 and helped the company grow from $1 million in ARR to $250 million in ARR.

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