Chad Malchow isn’t your typical sales executive. A man who never missed a day of high school, he’s spent the past 22 years mastering the art of sales in B2B, B2C, and B2D contexts across companies like McLane (supply chain services), The Hershey Company (chocolate), Kissmetrics (analytics), and Gitlab (dev tooling), where he served as CRO for three years.

He’s currently VP of Sales at Honeycomb.io, a monitoring tool that helps engineering teams understand their production systems through observability.

Like any leader in his field, Chad spends a lot of his time talking to people in meetings, sales calls, reviews, and coaching sessions. He also spends a lot of time crunching data - attempting to understand which messages resonate the most with the company’s audience, how to maximize the value of each sales deal, and how to increase growth.

Sales is both art and science. Mastering sales calls, for example, is an art; but listening to call recordings to spot areas for improvement is a science. As a big basketball fan, watching game footage is second nature to him, and he similarly obsesses over Honeycomb’s sales process to eke out every competitive advantage.

“In baseball, there’s batting averages. In basketball, there’s your shooting percentage. In sales, it’s win conversion or stage conversion. So, I try to apply all those and say, “Okay, where can we have the biggest impact for you as a sales rep or team?” - CM

As a sales leader, Chad’s biggest challenge is aligning sales methodologies and tools into a cohesive strategy - a requirement for most growth-phase startups trying to optimize their sales cycle performance.

In Chad’s view, getting buy-in from the entire organization requires a clear understanding of ‘why’ the company is taking a specific approach and how it will ultimately benefit the organization. He credits a TED Talk from Simon Sinek on this philosophy:

“When people are bought into the why, why we’re doing stuff, it doesn’t matter how you do it or what you’re doing. So, that really resonated with me, and I use that today and often.” - CM

Right now, Honeycomb is focused on nailing their proofs of concept and leveraging ‘Command of the Message’ - an attempt to understand their customers’ current states and challenges. This initiative helps Chad and his team flesh out their product’s technical requirements and align them to desired business outcomes.

The future of post-pandemic sales: building an effective sales culture

The pandemic changed the nature of sales, but one thing Chad is sure will persist is ‘selling on value.’ Sales teams spend much of their time understanding an organization’s needs, urgency, and budget (see our MEDDIC guide for more info). Linking their needs to your product is what determines sales success.

“Selling on value is going to be key. Having a great product is going to be key. I don’t think those will ever change.” - CM

One negative result of the pandemic’s isolating effect was people asking the same questions in meetings, sales coordination calls, and digital channels. Honeycomb was already planning to go remote before the pandemic hit, and with distributed teams came the need for cohesive, centralized communication.

One solution Chad recommends is documentation: creating text resources on common tactics and sales plays that teams can refer to when needed.

“I learned this at GitLab. GitLab is a remote-only company, [and] we had the discipline of documenting everything and helping point people where to find the answer.” - CM

While this asynchronous collaboration approach is a net positive for many companies, companies can still get a lot of value from brainstorming together, setting up 1-on-1s with colleagues, and hosting online training sessions.

“We just did a sales pitch where everybody got together and practiced the sales pitch. So typically, you go into the room, you have people go up, you can do role-playing. Well, now we just use Zoom. We have all different people do this and learn from it.” - CM

More importantly, companies need to foment a culture that implicitly supports remote working - for example, by giving remote workers equal airtime in meetings, looping them in on important decisions, and encouraging online get-togethers.

Honeycomb’s sales tech stack

Honeycomb uses a bunch of tools to maximize the efficiency of its sales, including:

• CRM: Salesforce
• Email outreach: Outreach.io
• Session video recording and playback: Outreach Kaia
• Business Intelligence: ZoomInfo
• Social selling: LinkedIn Sales Navigator
• Document management: DocuSign
• Meeting scheduling: Calendly
• Deal room management: Momentum

What to look for when hiring a great salesperson

Having been involved in a few hiring rounds in his career, Chad has seen his fair share of hopeful candidates and has developed a keen sense of who would make a great addition to his team.

One standout quality in any candidate is curiosity. Asking the right questions shows proactivity, foresight, and genuine interest in the organization and role. Bonus points if those candidates relate their questions to the company’s recent initiatives and announcements.

Another quality he looks for - and one he admits he is still working on - is empathy. The success or failure of a sales team is partially influenced by how empathetic their reps are to a prospect’s problems and how effectively they communicate with all parties involved.

“We always think we can communicate well, but we can always do better.” - CM

On the flip side, there are some red flags that instantly set off alarm bells about a candidate. For example, candidates who talk about how much money they’ve brought in - without providing specifics - are a huge red flag.

“Salespeople, marketing people, they’re usually really good at creating a cloud and a little vapor out there. So, I want to get into the specifics and understand how you’ve done something, not just what you’ve done.” - CM

Chad also believes that the nature of remote sales largely negates the need for boisterous, extroverted personalities and welcomes introverted, tech-savvy salespeople.

“Sales is happening within Slack, email, and Zoom. You no longer have to be on a stage or a big room, which a lot of introverts might find overwhelming.” - CM

Chad has an enduring respect for sales development reps, whose job - cold-calling prospects for profit - is an often long, grueling, and thankless one.

Tech, however, can lessen the workload and streamline sales workflows. Sales teams should hire reps and sales engineers who understand sales tech, use it proficiently, and track trends. This might involve mastering CRMs like Salesforce, wrangling remote communication tools like Zoom and Calendly, and using deal room tools like Momentum to close enterprise sales.

“I need people who are using the [latest] sales tools consistently. If I can find a person who can implement tech into the sales stack and understands how it all works together, that’s great.” - CM

Such people are generally biased towards action, choosing to do what’s best for the company without first seeking permission. However, such traits need to be paired with high integrity on the rep’s part and implicit trust from their team.

On personal productivity, retirement, and SDR career advice

Chad’s formula to getting work done is deceptively simple: block time off to do stuff. For a role like his, this might seem impossible to pull off, but he insists on two things: avoiding the monotony of meetings and writing things down.

“To me, if it’s not written down on my calendar, things can get missed. I need to have things written down to commit to and hold myself accountable.” - CM

If Chad wasn’t in sales, he’d be coaching youth basketball. A father of three boys, he has coached them and other kids in almost every sport imaginable, from basketball to baseball and soccer. He can’t ever see himself retiring from sales or starting his own company, but he hopes to continue advising companies on their growth and sales strategy in the future.

His one advice for new SDRs? Get into tech sooner. His first few jobs weren’t in the tech industry, but early exposure to sales tech would’ve given his career a massive boost. He also advises reps to join companies with the right learning resources, tools, mentors, and a failure-friendly environment. Of course, not all reps have such options, but company leaders can play a role in improving the environment in which new reps begin their careers.

You can connect with Chad Malchow on LinkedIn and Twitter.

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