Celebrate the Hang-Ups as Battle Scars
A Few Lessons on Cold Calling
Switching to B2B meant rethinking our entire sales approach. With our runway dwindling, cold calling emerged as the most direct, affordable path to start filling our pipeline. I drew motivation from Jim Koch's origin story hustling Samuel Adams door-to-door despite his fancy Harvard pedigree. If a BCG consultant could do it, why couldn't I dial for dollars?
I wasn't very good at it, but desperation is the mother of reinvention. With a looming "sell or perish" attitude, we somehow signed an office client. Then another. Before you know it, we had 17 new customers in 3 months and 56 within 6 - with over 75% from those relentless dials.
Looking back, here are some key lessons I learned about effective cold calling as a scrappy founder:
Time is Precious: Hang Up Fast to Talk to More Real Prospects. The average success rate of cold calling ranges from 2%-5%. When I first started, I only got to speak with 2 people in a 2-hour block and none of them wanted to talk to me. After some painful hang-ups, I realized a startling 80% of dials were dead ends like wrong numbers and voicemail loops. By hanging up first, I could connect with 5-6 real prospective leads per hour instead of wasting time."
Time it Right: The Right Call for the Right Person. Office managers were most chatty and open on Thursdays before holidays like Thanksgiving - who isn't dreaming of the weekend after the Monday blues and Tuesday grind? We learned this by limiting your daily cold calling duration. Going full tilt could easily burn through all your leads with nothing to show for the exhausting effort. Doing smaller batches allowed me to run little experiments too - judging lead receptiveness and identifying which days/times worked best. In the end, we primarily focused on Wednesday 3:45 PM and Thursday 3:30 PM calling blocks.
Use Data to Overcome Irrational Calling Fears. My irrational dread often started well before the first dial, triggered by memories of recent hang-ups and rejections. But I learned to squash that negativity by treating it as a data-driven experiment. Obsessively tracking metrics like contacts reached vs. voicemail robots kept me focused on the numbers, not dwelling on emotional highs and lows. That data became my security blanket when doubts creeped in. After all, I only get 1-2 hang-ups per month, hardly worth dwelling on.
BONUS TACTICS:
How to Start a Call?
"Hi, this is Trista from KitcheNet. Would you be open to chatting about office fruits for a minute?"
While many websites regurgitate the same advice on magical opening lines, we found straightforward casual openers worked best for us.
Establishing context through warm intros also helped a lot.
“Hi, Jim from your office told me to talk to you, he enjoyed the golden Kiwis at the lobby and mentioned we should chat about office fruits.”
“I was at your office for an event last week, and the apples on your counters caught my interest, how do you like your office fruit suppliers so far?”
Not Every First Call Needs to Be a Hard Sell
Instead of aggressively pitching, our goal was engaging prospects through consultation - demonstrating our deep expertise in unique, fresh fruit varieties and our seamless service experience.
"This week's star? Golden kiwis tasting like as if strawberry and pineapple had a baby...paired with snappy green grapes!" Rather than reciting features, we brought the rotating seasonal selections to life through vivid descriptions from our knowledgeable produce gurus.
We positioned ourselves as advisors by addressing real office issues our service could improve - reducing food waste, offering healthy snack novelties, and simplifying managers' weekly snack coordination.
If prospects seemed genuinely interested and talks about their challenges, we could offer an on-site tasting to provide an immersive firsthand experience before any commitment. We avoided forcing pitches on the disengaged to avoid wasting time and services. Ultimately, these golden kiwis aren’t cheap.
Celebrate the Hang-Ups As Battle Scars
The key was celebrating "battle scars" as signposts of progress:
Getting hung up on showed a valid number, just not the right time.
Prospects already having a service confirmed the need existed.
And any expressed interest was a success to build upon.
By reframing milestones big and small as learning opportunities, cold calling stopped feeling like throwing darts in the dark. Instead, it became a iterative process I could intelligently refine based on what worked and what didn't with each cycle.
I was never a natural at cold calling. As an English-as-a-Second-Language, I always overthink. By embracing a learning by doing mentality, I turned it into one of our most potent growth engines. Simple tools like a Google sheet, a phone, persistence, and a thick skin were all the firepower required.
Hi,
I'm Trista. I ran a social enterprise that delivered office fruit subscriptions to help address food deserts in Chicago. Now I write about my experiences, because I believe these scrappy stories are interesting and can inspire others.
If you've read this far, I'd love to hear your thoughts! Even a simple "gobanana!" in the comments would provide huge motivation for me to keep writing.
I'm also very interested in learning what other sales or cold calling topics you'd like me to cover next.
Thank you so much, and have a fruitful day!
Gobanana!
Amazing tips!!! ❤️🔥💯