I’m Kayla. I lead sales at a small B2B software shop. Twelve reps. One loud coffee machine. Too many tabs open. You know how it goes.
Skip straight to the full case study if you’re skimming for the punch line.
Last year, our sales process was a mess. Deals slipped. Notes lived in heads. Hand-offs were shaky. I tried to fix it with “sales process optimization.” Sounds fancy, right? It wasn’t. It was mostly hard talks, sticky notes, and a squeaky whiteboard.
If you want a deeper rabbit hole on making processes lean, check out the playbooks on Optimization World — they cut through fluff. To get my bearings, I bookmarked a short list of resources—including this concise roundup of sales best practices—and cherry-picked a few that felt doable for a 12-rep shop.
Here’s what I did, what blew up, and what really helped.
The Day I Knew We Needed Help
I lost a good deal because we took 19 hours to reply to a warm lead. That email sat. I kept thinking, Eh, it’s fine. It wasn’t fine.
I felt sick. I still do a little. So I made a plan.
Step 1: Map the Path (and Cut the Junk)
I wrote our stages on a whiteboard. Lead → Discovery → Demo → Trial → Legal → Closed. We had two extra stages: “Interested” and “Verbal.” Cute names. No use. I cut them.
Want to see another take on straightening out chaos? I got a ton of ideas from this messy workflows teardown.
Then I set rules. To move to Demo, we need pain, timeline, and buyer. No guesswork. No vibes.
Funny thing? Reps first groaned. Then deals moved faster. Like a grocery line that stops zig-zagging.
Step 2: Speed Wins, Every Time
I hooked HubSpot to Slack. The core ideas came straight from HubSpot’s own sales strategy playbook, which hammers home how a quick first touch can set the tone for an entire deal. New lead in? Ding. We aimed for a first reply in under 60 minutes. We dropped from 19 hours to 47 minutes in week two.
Speed isn’t just for inboxes—you can see how a simple tweak shaved seconds off page loads in this ClickFunnels page test.
My first win came from a VP who wrote, “Thanks for being fast.” That deal closed in 11 days. Before, our average was 41 days.
Step 3: A Simple Discovery Checklist
I love winging it. Also, I kind of hate it. So I made a one-page guide for the first call. Five things only:
- Problem in their words
- Who signs the deal
- What a win looks like
- Key dates
- Deal blockers
Two questions did the heavy lifting:
- “What happens if this slips a month?”
- “Who else will say yes or no?”
Average call time went down by 8 minutes. Close rate went up 7 points. Wild.
Step 4: Listening to Calls (Yes, It’s Painful)
We used Gong to review calls on Mondays. I set one simple rule: talk time below 55%. Our baseline was 72%. Yikes.
I learned I cut people off. A lot. After four weeks, our win rate moved from 18% to 26%. Not massive, but real.
One more note: hearing your own voice is rough. But it works.
Step 5: Email Sequences That Don’t Sound Like Robots
We used Outreach for a five-step sequence:
- Day 1: Short email with one problem they might have
- Day 2: LinkedIn note
- Day 4: Voicemail and a one-line email
- Day 7: Case snippet (no fluff)
- Day 10: Breakup note, kind but firm
If you're curious how another team dialed in email conversions, the ActiveCampaign split-testing play-by-play is worth a skim.
Good subject line: “Still wrangling month-end?”
Bad one I wrote (and regret): “Quick synergy touchpoint.” I cringed as I typed it. Response rate was 0.6%. I deserved that.
Step 6: Fix the SDR → AE Handoff
SDR sets the first meeting. AE runs it. Easy to say. Hard to do.
We made a tiny handoff note with five fields:
- Problem
- Buyer
- Date
- Tools they use now
- Why now
Before this, I started a call cold and asked, “So tell me about your team?” They already told us. Not a good look. That meeting ended fast. After we fixed handoffs, no-shows dropped by 40%.
Step 7: One-Page Pricing Beats Custom Quotes (Most Days)
We sold small deals with a one-page sheet. Three tiers. Clear limits. No “Let me craft something special.” For mid-market, we still did custom.
I partly stole the courage to be blunt about prices from this split-tested pricing experiment.
A 15-seat deal closed in two days after we sent that sheet. Simple wins.
Step 8: Calendar Links Are Your Friend
We used Calendly. One click from email. Two clicks to book. No back-and-forth.
One CFO wrote, “Thanks for not making me hunt for times.” That note lives in my head rent-free.
Step 9: Lead Scoring, But Chill
I first built a huge model in HubSpot. Too many rules. It broke. Reps stopped trusting it.
For the analytics nerds, the Mixpanel split-test deep dive shows how event data can guide those five rules.
So I cut it to five:
- Job title match
- Company size fit
- Viewed pricing page
- Booked a demo
- Used our free tool
That was enough. Meetings got warmer. No magic. Just tidy.
Step 10: Better Recap Emails
After each call, I sent a recap:
- Your problem: “Late reports, missed data.”
- Our plan: “Automate two feeds, 2 weeks.”
- Price: “$X per month”
- Next step: “Docs by Friday, demo for ops on Tuesday.”
Short and clear. One buyer replied, “Thanks, this makes it easy to move.” That line? That’s gold.
Bonus: Legal and Security Without Tears
We kept answers to common security questions in a doc. SOC 2? Check. Data flow? Check. We shaved six days off legal for bigger deals. Six days is a lot.
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What Flopped (So You Don’t Repeat It)
- Too many stages. We had nine. No one followed them. We cut to six.
- A contest for “most calls.” Reps speed-dialed and burned leads. Oops. We switched to “qualified meetings” instead.
- A 30-field deal form. Fields sat blank. I kept five. Now they’re filled.
I had to say sorry more than once. Change is messy. People matter more than flowcharts.
Tools I Used, Warts and All
- HubSpot Sales Hub: easy workflows, reporting is decent, dashboards still lag at times.
- Gong: call reviews are strong; the app can feel heavy on slow Wi-Fi.
- Outreach: great for sequences; setup took me two long nights and a lot of tea.
- Calendly: simple, clean; some buyers hate links, so we still offer times by email.
- Loom: I sent short recap videos; watch rates were high for deals over 10 seats.
None of these tools saved us alone. The process did. The tools just helped us stick to it.
The Results (90 Days After)
- First reply time: 19 hours → 47 minutes
- Close rate: 18%