Weekly roundup
Week 1 of Q4. Clean slate. If September was the warm-up October is where we set pace
We wrapped our first monthly comp, kicked off Apollo provisioning and sharpened a ton of cold call + email plays in office hours
Now we use it
Here’s what happened and what to hit this week. 👇
Announcements
🏆 September Contest — Winners
Huge congrats to the crew that logged and competed in September
1st: Erica Stacy-Tarwater — 25 meetings (HeadsetAdvisor headset on the way)
2nd: Dustin Javaherian — 7 meetings
3rd: Evan Edwards — 2 meetings
New month, clean board
We’ll keep recognizing movers all October—prizes pop back next month
→ Submit your October numbers (takes <60s) https://undergroundleaderboard.notion.site/26fc6a270e4a811f8fd8c894b0afbb26
🔌 Apollo | First batch live this week
We start provisioning the first cohort on Oct 6. Missed this wave? No sweat we’re doing new sign-ups in two-week batches. Watch Slack today for the short claim form
Already have Apollo? We’ll share add-on perks for existing users in the same thread
🧰 Help me pick the next partners
We’ve got Apollo, ConnectAndSell, Sybill, Sendspark in the stack.
What do you wish you had access to (or can’t live without)? Reply to this email (or drop in Slack) with your top 2–3 tools. I’ll go hunt the deals for the Underground
The Playback (last week)
Tuesday | Cold Call Office Hours (recap)
We went deep on enterprise conversations, agenda-led calls and tighter discovery. A few big hitters
Keep cold calls 6–10 mins max. Earn the next block don’t wander
Lead with persona-specific questions. (Map the account, craft one opener per role)
Assumptive close with times. Offer two slots. Put a brief agenda in the invite to boost show rate
Workshop: Objection handling reps + using incentives only as a last nudge
Action pack for this week
Build 3–5 discovery questions for each persona you call
Add a 2-line agenda to your calendar template
Practice a 60-second close that lands two time options
Wednesday | Cold Email Office Hours (recap)
Theme: short, specific, multi-channel
Soft CTAs win: “Worth a 10-min look?” / “Want the 90-sec video?”
Use receipts: tie to role, site snippet or recent signal
Have fun: memes/GIFs in later touches still work (Erica pulled 55 meetings during COVID with this move)
Tooling: we outlined how to use ChatGPT well (feed it screenshots + wins; cap emails at ~120 words)
This week’s micro challenge: rewrite one live thread with a soft CTA and send 3 time options in the follow-up
Thursday | Social Selling Office Hours (recap)
Social Selling hour was canceled (family stuff). We’re back on schedule this week
Events This Week (all @ 12:00 PM PT)
Tuesday – Tuesday Taps (Cold Call Office Hours)
Live roleplays, opener surgery and objection handling until it’s cleanWednesday – Write It Right (Cold Email Office Hours)
Subject line clinic + soft-CTA rewrites. Bring one thread we’ll fix it togetherThursday – Tactical Thursday (Social Selling)
DM ladders and content that converts
comment → save/share → DM → micro-offer
🌟 Member spotlight
Let’s give it up for
Omair Masood 👏
Fresh grad out of Rutgers Business School (B.S. in Supply Chain). Paying founding member, back in the SDR grind, actively prospecting hiring managers and iterating fast
He’s been in office hours, rebuilding messaging with the crew (shoutouts to Max + Victor) and pushing daily.
If you’re hiring or can open a door DM Omair. The man is coachable, consistent and hungry
Got someone to nominate?
🎯 Tactical Corner
1) Cold call opener (30 seconds to earn 30 more)
“Hey __, Tom here. I’m calling about [specific thing you saw] caught you between meetings?”
If yes: “Quick one: When [persona] is trying to [problem] are you using [current approach] or something else?”
Goal? Relevance → permission → one targted question → book the next block
2) Email follow-up that gets replies
Subject: quick one for role
“Saw signal. I can share how peerpeerpeer cut X by Y% want the 90-sec overview or should I just send 2 time options for this week?”
Soft choice. Lower friction. Multi-channel with a LinkedIn touch.
🥷 The Stash (perks you can claim)
Apollo — cohort 1 starts Oct 6 (two-week waves after). Claim form in Slack today
ConnectAndSell — up to 10 hrs/week parallel dialing
Sybill — 3 months free (AI notes + call insights)
Sendspark — up to 12 months free (video selling)
Want access? Reply to this email or DM me in Slack and I’ll get you set up.
One ask before you bounce
Tell me which tools you want next (dream picks welcome). I’ll go chase the partnerships and perks so our stack stays unfair
Q4 starts now. New board. New momentum. Let’s stack wins
— Tom
