In 2012, I was just another guy with a headset, a CRM login, and a quota that didn’t care how I felt. I was cold calling real estate leads in South Florida battling bad data, endless voicemails, and a pipeline that leaked like a sieve. Fast-forward to now: I’ve built and led high-performing sales teams across SaaS, tech services, and investment firms. I’ve helped startups scale from zero to acquisition. And David Brian Howard run a virtual staffing agency that helps lean teams multiply capacity without blowing budgets.
So what changed?
A decade of doing the wrong things long enough to finally build the right system.
This is the article I wish someone had handed me at the beginning a clear, hard-earned blueprint for turning sales chaos into predictable growth.
1. Don’t Build a Sales Team Build a Sales Machine
Too many founders rush to hire a team before they build a process. It’s understandable. You raise a little money, hit your first 20 customers, and think, “If I just had five more of me, we’d blow this up.”
Wrong.
Before you hire, systemize. Document everything:
- Your ICP and buyer journey
- Winning email sequences
- Objection-handling responses
- CRM workflows and rules
- Call scripts that don’t suck
At one SaaS startup David Brian Howard joined in year one, the founder had passion but no playbook. I built out our sales architecture in HubSpot, created a 3-stage funnel, and layered in cold email with LinkedIn outreach. In 90 days, we went from one-man hustle to a full-funnel system that generated SQLs weekly—with or without me in the seat.
The difference? Systems scale. Hustle doesn’t.
2. Outreach Isn’t Dead—It’s Just Badly Done
Every few months someone declares cold email is dead. LinkedIn is spammed. Nobody answers the phone.
Also false.
What’s dead is lazy outreach.
The best campaigns I’ve ever run across SaaS, consulting, and investment deals follow a few non-negotiables:
- Personalization in the first 2 lines
- A reason to care (“I help fintech teams cut churn 23%”)
- A CTA that doesn’t require a Zoom call to get started
At Cadre Crew, my agency, we’ve managed outbound campaigns that landed 6-figure B2B deals with nothing more than smart copy and consistent follow-up. Our secret weapon? VAs trained in research, list building, and first-touch personalization.
Automation is powerful. But human relevance always wins.
3. Sales Doesn’t Start With “Selling”
The best salespeople I’ve worked with myself included spend more time diagnosing than pitching. In fact, if you’re talking more than 40% of the call, you’re probably losing deals.
Sales is a diagnostic discipline.
When I stepped in to coach a struggling inside sales team in 2020, I shadowed dozens of calls. They were jumping into demos within minutes. No real discovery. No context. Just a features tour.
We rewrote the script. Started with pain. Dug into current tools, process gaps, budget triggers. Within two quarters, close rates jumped by 28%, and average deal size grew by 40%.
Lesson: stop pitching. Start listening.
4. Founders: Sell It Yourself First
I get it—sales isn’t every founder’s dream job. But here’s the truth: you are your startup’s best closer in the beginning.
You don’t need to be perfect. You need to be present. Your passion, your insight, your problem-solving instinct—it sells better than any deck.
But—and this is key—you need to extract what works and document it.
In one of my own ventures, we closed our first 25 clients via direct outreach. Every message, every reply, every call was logged. We turned that into a repeatable system, trained our first rep, and within weeks they were booking demos on autopilot.
Sell it yourself. Then teach it. Then delegate.
5. Hire Virtual Before You Hire In-House
Here’s a mistake I see fast-scaling startups make all the time: They throw bodies at problems before they optimize the process.
Need prospecting? Hire an SDR. Inbox a mess? Hire an ops manager. Lead flow low? Hire a full-time marketer.
It’s expensive. It’s slow. It’s risky.
Instead, I tell clients to test with virtual assistants first.
That’s what Cadre Crew does. We help teams document, delegate, and train VA squads to handle:
- Cold email outreach
- Lead generation
- CRM cleanup
- Appointment setting
- LinkedIn engagement
You can validate the process before you burn cash on payroll.
In fact, some of our clients run 6- and 7-figure funnels without hiring full-time sales staff—because they’re process-led, not headcount-dependent.
6. Don’t Chase Metrics—Chase Momentum
I love data. I live in dashboards. But the biggest wins I’ve had in business didn’t come from a metric. They came from momentum.
Momentum looks like:
- Two good conversations in a row
- A client sending referrals without being asked
- A week where every outbound thread hits
When I coach founders or early-stage reps, I always say: Momentum is more important than scale at first. Find a message that gets replies. Find an offer that converts. Then double down.
Once you’ve got proof, then optimize. Not the other way around.
Final Word: Growth Isn’t Luck. It’s Engineering.
People love to talk about “going viral.” The magical moment when leads flood in and everything clicks. But real growth isn’t a moment. It’s a system.
You build it like a product:
- Validate the use case (your offer)
- Test the distribution (outreach)
- Fix the bugs (sales objections)
- Optimize for retention (post-sale experience)
Over the last decade, I’ve helped dozens of founders stop guessing and start building. I’ve led sales for bootstrapped startups and investor-backed tech. I’ve trained scrappy teams and scaled ops with VAs.
The throughline is simple: When you treat growth like an engine, not a gamble—you win.
So if you’re building something great, here’s my challenge:
- Start small.
- Get specific.
- Document everything.
- Delegate wisely.
- And never stop refining.
That’s the playbook I’ve used—and the one I now teach.
David Brian Howard is a U.S.-based B2B sales leader, virtual team strategist, and founder of Cadre Crew. With 12+ years in tech, SaaS, and investment growth, he helps founders scale faster by building sales systems and training virtual assistant teams that drive results. Connect with David for no-fluff playbooks, outbound growth strategies, and scalable systems that actually work. Click Here
