After serving more than 150 sales teams and collaborating with some of the best (and the worst) sales leaders, I wanted to summarize ten of my greatest takeaways from Tim Claudin, the VP of Sales at Balto here in St. Louis. Tim and I grew up in startup sales and in ten short years, our experiences have shared interesting similarities and differences.
One of our recent small group sessions during Pavillion’s CRO School focused on the DNA of good sales leaders and contributors. While I’ve worked solely with growth-mode sales teams, it’s been my experience that the best sales leaders are the ones with quirky, funny, and obsessive personality types or completely random backgrounds.
Tim, a transplant from ministry and youth ministry at that, falls into the latter category above. So if you really think about it, there’s no surprise that he’s a great communicator with an endearing honesty that pairs well with his servant leadership.
Tim and I during one of our coffees.
My coffees with Tim are very important because they feed more than my professional mind—he’s also hilariously good for the soul and keeps me grounded on what’s really important. Over the last several months, we’ve met, shared, and collaborated on the challenges we’re experiencing as practitioners and consultant advisors. I leave each time thinking Tim is one of the greatest, unsung heroes of our industry. So, I decided to capture my favorite parts of our conversations and share them with you. Here are my favorite takeaways from my time with Tim - #10 is my favorite:
1. Be a student, not a know-it-all. And keep it fun too.
Tim frequently talks about the LinkedIn practitioners he loves and follows, even saving their posts to his desktop to implement personally, as well as the several books that have shaped his personal sales techniques and leadership. He often jokes that without Prison Mike from The Office, there’d be no chance he survived in sales.
2. A good leader believes when no one else does.
The state of sales is hard enough, even more so in today’s economic downswing and the undeniable stress it’s putting on young tech companies. Whether big organizational decisions consider their sales leaders or not, they are undeniably on the forefront of feedback, grief, panic, and overzealous excitement from their team. Sales reps must stay focused and believe the leader they support supports them back. When sales leaders are broken, so are their teams and their processes, and the results will not come. Since sales can be tumultuous, it’s important to put your trust in a sales leader who believes in their team and mission.
3. The minute you recognize a pattern, in behavior or metrics, address them.
Do not wait till the end of the quarter to address an issue! It’s important to continuously serve your team and push them. Know how to motivate them and dedicate time for the hard conversations. Tim shared with me that his team is fully aware that he’s a straight-shooter (apparently bordering on being a jerk). Addressing any issues immediately tells your team, “I am here to serve you and sell alongside you all the rest of the week, but in this 30-minute 1:1, I will be hard on you because I care and want you to succeed.”
4. Teach your reps to care. Like, really care.
How can a young sales rep relate to the things keeping C-level executives up at night? Bring in trusted advisors, create a safe ecosystem of business mentors, and encourage your sales reps to discuss and hear firsthand the mission behind sales. After all, if you're selling a product that truly solves a real problem, the sales process organically executes. To quote Tim, “SaaS sales is serving when done right”.
5. Personal systems are boring but make the difference between good and great.
New hires often bring their own personal systems, ways to stay organized and work efficiently. Even if these systems have worked in the past, we’re silly to think they’ll apply perfectly to a new company, position, targets, tech stack, internal expectations, and well, new everything.
Even with my own team, there are major learning curves to finding the system that will work for them. It can take months for them to find their groove and achieve success. Far too often, this is detrimental to onboarding. We often just train sales reps on the CRM, hand them an onboarding handbook that introduces them to the company, and maybe run a few 1:1s with members of the team.
But how powerful would it be for leadership to identify the personal systems of the top performers, then share them with new hires? Imagine a sales leader learning what their top contributors do each morning, how they prep for their calls, how they calendar block, how much time they research, how they execute follow ups to their main POC vs the full buying team, how they prep for the pipeline reviews, how they wrap up each day and prep for the next…
This knowledge is the difference between good and great. These are the things that sales leaders don’t want to teach, shouldn’t have to teach, and don't have the bandwidth to teach. In most cases we won’t, rather relying on the new hire’s own grit and determination.
And while a big part of me believes that a new hire needs to do the work to figure it out, I hate the idea of learning something twice. If we can learn and share more early on, maybe it will only take 90 days to onboard a new hire, eliminate sunk costs on bad hires, cultivate a stronger team culture, build trust early, improve performance… and maybe turn the good into great!
6. The differences in selling to SMB and Enterprise go beyond the strategy.
Selling to SMB vs Enterprise needs to be measured differently with separate pipelines because these prospects convert differently and require different exceptions. These pipelines should be reviewed differently and deserve their own meetings if not their own sales reps.
This, however, does not mean that marketing cannot support them the same way, but that their influence and impact will be different. I personally love supporting a quickly moving SMB pipeline while warming up the long-game with large accounts for the Enterprise pipeline. Most companies can't afford to do only one—thus, a strategy for each and a machine for both are essential. But as Tim often reminds me, once you have a good pulse on what a good customer looks like, let that dictate the effort and focus on one target type vs another.
7. Bad news early isn’t bad news.
Sales is creative and measurable, thank God. It’s the addictive part about it for most of us. But when we dangerously convince ourselves that things are always good, it eliminates opportunities for the team to support you and creatively solve objections, damaging trust internally and with the prospect.
You’re never selling something your prospect flat out does not need, so if there’s a roadblock or unforeseen complications, “Do not suffer in silence, call the calvary,” as Jim Eberlin, our former boss and the Founder & CEO of TopOpps, would always say during forecast calls.
8. Build the sales process with customers in mind.
An effective sales process isn’t about internal checks and balances—the purpose is to keep ourselves organized, honest, and collaborative so we can solve the needs of our customers by better serving them during the discovery phase of our partnership. Like a motor to a car, when it’s not humming along on all cylinders, it will eventually crash and nothing will be operable. Care for the sales process, believe in it, stick to it, rely on it, refer to it, and keep it at the center of all your reviews. Lead by example and cling to it like the pulse or bible of your sales organization, because it is.
9. Sales and marketing leaders need to talk weekly.
Help marketing serve sales. The “us vs them” mentality is for the weak sales leader and I am thankful we see less and less of this now. When your sales leadership can measure the “assists” they get from Marketing, whether directly from a form fill demo request or indirectly with supportive content nurture through an established sales opportunity, they can collaborate.
Oftentimes, the marketing team is starving for feedback and requests from sales to make their tactics more effective. Every sales and marketing leader talks the talk of partnership and collaboration, but very few have the systems in place to strategically grow their undeniably important relationship.
10. Live in reality, no matter what.
After working with a multitude of salespeople in my career, I've identified some themes I've validated with Tim over our coffees. The biggest one he credits to his success is simple: living in reality.
Far too often leaders, or even an entire company, find themselves obliviously bought into their own hype. This has always been alarming for me when I start to serve a sales team with a dreamer sales leader. They appear to ignore the data that rolls up to support sales goals or they are tone-deaf and lack accountability to the actual work it takes to build the rocket ship they think they're already on.
Tim is notoriously and intrinsically honest - he keeps core metrics accurate and communication strong throughout the entire sales period, not just at the end. His weeks are stacked with internal meetings led by accountability and deal inspection. This keeps truth in the numbers, ownership of the reps, and collaboration with leadership where they need it most. The tenured leader knows how difficult this is - these little things are really, really big things - because most people who have "been there, done that" don't want to do “that” again.
Every strong up-and-comer I've met does the little things really, really well. Tim manages his reality well because of his diligence, attention to detail, and management rigor. This is the biggest and final reason I adore his leadership.