Becoming a Cybernetic Rambo

It’s no secret that prospecting sucks. It has become increasingly more scientific in execution, with bookings lower than ever.

The technology landscape has matured so intensely over the last few years that we’ve effectively entered into a paradoxical reality of Mass Effect & Star Trek but with AI SDRs carving out a dystopian battleground.

Like, we’re in the future bro.

We’re living in a Cyberpunk future filled with everyone peddling subscriptions. Everyone apparently can cure your B2B cancer and there are loads of terrible ChatGPT reskins that really don’t solve shit.

If you’re still prospecting like a dinosaur, you’re not hitting quota. Not this year.

Out of around 143 dials I did the other day, 46.75% of my time would’ve normally been spent listening to voicemails of old white dudes or generic robot greetings.

Can you imagine actually listening to 72 voicemails? How long would that take manually? Easy hour, right?

Fuck that honestly. Ain’t nobody got time for that.

And influencers who don’t sell anymore telling you to do hyper research and manually dialing, 100% aren’t consistently actually rolling up their sleeves and dialing themselves.

While you will absolutely have better conversations on a 1:1 level, mentally, do you have the bandwidth to do that for months on end? Without burning out?

Truth is, sales has become catatonic and robotic. At least as it relates to top-of-funnel shenanigans. There’s less humanity in the process and it’s more about raw optimization.

You can fight me about it but the old methodologies aren’t sustainable, not for our mental health. It’s become this festering and rotting blight and an increasing reason why SDRs are turning over ≈18ish months.

Why do you think hunter based skills are so in demand? It’s not that nobody can cold call, it’s that cold calling and prospecting is a drag. It’s soulless.

I’m lazy dude. I just want to mentally check out, press a button, and have more conversations. Spray and pray all day, son.

That’s the dream! And truth be told, it doesn’t need to be a fantasy. And it certainly doesn’t have to be based on a hope and a prayer. I’m going to give you the step by step playbook on how to be that beautiful lazy SOB quota crusher you were born to be…

Caution — While this is extraordinarily potent — This takes work to set up and it may mean you can’t run maverick without the blessing from your org.

Recommended tech stack

1. BearWorks (Parallel dialer for cheap)

2. SendSpark (AI videos for easier prospecting)

3. Paage or Aligned (For champion enablement, triggers, and providing more education for prospects)

4. Clay (Swiss army knife for pulling multiple data tools under one roof)

5. RB2B (Deanonymize website visitors for cheap)

6. ZoomInfo/Apollo/Seamless (Contact data for obvious reasons)

7. GPT4o/Gemini/Claude Sonnet 3.5 (For sifting through longer research)

8. Chorus/Gong/Fathom (Mostly for the transcriptions to feed to my AI)

Again, some of these tools aren’t practical if your company isn’t aligned (heh) with your strategy. Without justification to your leadership, some balk at the idea of change because it’s so radically different than what they’re doing. And without proper integrations, your leadership won’t have visibility into what you’re doing.

SO TALK TO THEM and build out an action plan to set proper expectations.

Or smash quota and ask for permission later, whatever. I’m not preaching the gospel here but my personal tech stack budget is literally $179 a month, so you’re not exactly breaking the bank.

Prospecting on steroids

1. List Building - Message Market Fit

You might want to invest in a VA (you can find them for cheap on Fiverr or UpWork) but a strategically baked list solves the spray and pray woes.

The idea here is to think like a marketer. We’re NOT casting a wide net, we’re getting ultra granular to the problem we’re solving.

Slice and dice by things like Industry —> Company size —> Revenue —> Headcount Growth —> Organize by Intent categories (it’s not hocus pocus if you aren’t using dogshit). Each industry, each segment, each whatever will have it’s own list.

If you care about technology that company is using and that information is public, that’s another list.

Next, we’re gonna filter again by persona. You’re making a separate list for each persona.

Then you’re slicing and dicing AGAIN by filtering those contacts with those you have ACCURATE contact data for (Mobile #/Direct #/Business Email/Etc)

This might look like…

CISOs who work in Cybersecurity with a company size of 100-500 with a 10% growth in headcount YoY who are currently using Okta

That messaging you curate will be ultra specific to the people you’re talking to, yeah? Not hard to craft a relevant message when you’re ultra specific to their situation.

There are exceptions to this rule, however; some generalities can’t always be assumed. And your solution can be extremely complex, in which case a shotgun approach MAY NOT work for you. Like if I worked at Oracle, these dudes sell like 300 products. But even then, you can still safely make assumptions about the profiles you’re solving for. At least vaguely.

2. Build out RELEVANT messaging based on PAIN

If I’m calling folks with a super specific problem I’m solving for, my list naturally will be small. This is a good thing because I am going to be mad relevant with my intention. The PAIN is extremely specific. You are going to lead with this pain.

If you’re calling a VP of Sales who works in Telecom — What problems would this guy likely have? What initiatives is he likely working towards?

Come up with 3 core problems around that pain, that’s your entire outreach campaign. Each pain point can have it’s own messaging attached. Even better if you can figure out an initiative.

If you’re stuck at this, go through Chorus/Gong take those transcriptions of sales calls and feed them into AI, summarize the pain points of the specific personas and poof, now you have a talk track.

3. Enrich the data

Plug the data into Clay to validate your list. ZoomInfo/Apollo also do this but there’s limited credits. Services like SureConnect or PhoneReadyLeads can help steer you to who has the highest propensity to pick up the phone, increasing pick up rates. You also want to make sure the numbers and email are validated so you’re not spending calories calling losers.

4. Initiate the sequencing toolkit

After mapping out who I’m calling —> Developing the messaging that’s relevant —> And have some sort of observational context that was researched ahead of time by either me or my VA —> It’s time to start dialing.

My exact workflow starts by putting my list I’ve built into Bearworks. This parallel dialer allows me to dial 3 numbers simultaneously, or roughly 150 numbers an hour. It skips VMs, allows me to do AI assisted VM drops. And allows for integrations with Outreach/Salesloft/Apollo/Hubspot. And also filters through 5 different phone numbers, so my pickup rate is fairly consistent.

If someone doesn’t pick up —> They’re entered into a sequence. The sequencing is based on triggers of If [THAT] then [this]. Scout handles this well actually for email but is another tool.

VMs get auto dropped based on the list I uploaded and assisted with AI (basically telling the prospects name for me).

My first email I send with the subject: [Per my voicemail]

[First name],

Just dropped you a VM. Calling about [their issue, their initiative, whatever]. We solve that by [A, B, C].

Open to chatting?

The next step in my sequence is to first insert a follow up using SendSpark. Easy AI videos that uses their own website and name to come off as semi personalized. You could also just use a Loom and also say something like “Hey I made you a video about [X] talking about [Another observation], would you be open if I sent it to you? I worked hard on it 😀” and then make a video based on that. SendSpark isn’t relevant for non-software companies I’ve found, so might not be as useful. YMMV.

The next stage of my sequencing, I’ll send a Paage. I use this as an educational piece and also because maybe not everyone enjoys videos.

People process content differently, so I feel it’s important to use more broad strokes because we all gain value from things differently.

Your sequencing should be versatile. Again, some people like the phone, some prefer email, some like videos, some just want to click stuff. Your outreach should incorporate many different elements.

5. Bucket like a pro

Personally, I optimize my workflow by structuring my leads into tiers:

T1 → Contact immediately

These are people who have opened my email 3X [Trigger], have clicked on one of my links (bigger trigger), or have visited my website (Trigger).

You can see who visited your website with tools like ZoomInfo or RB2B.

Pick up rates from triggers are massive. T1 contacts I always manually dial. These contacts should be called ASAP. Set up notifications to hit Slack/Email/Everything. Time is everything here because they’re at their computer and available.

T2 → People who ghosted meetings previously

These people agreed to a meeting previously and we dropped the ball somewhere. Much higher chance to get a meeting on the books.

T3 → Closed/lost accounts from 6 months ago

Your software has undergone significant changes. Maybe new pricing was introduced. Maybe you have a new feature. Maybe their company priorities have changed.

More reasons to reach out.

T4 → Contacts who I never have spoken to

These people aren’t familiar with your number, haven’t received your emails. They’re cold and indifferent.

T5 → Contacts already on step 2 and above of your tasks

The chance a contact doesn’t pick up or engages with you becomes less and less productive the longer they’re in your sequence. After 21 days of being in your sequence without any success, set a reminder to follow up in 6 months. Not worth the effort personally, find someone else in the org.

Consistency over everything

Assuming you’re doing the above consistently, a chimp with a machine gun and very average skills will out-Rambo pipeline generation against the best manual workers. It’s not even close.

For raw numbers, just dialing for 2 hours a day, I can bang out a minimum of 300 dials. With validated and clean data and calling direct lines, that pickup rate should be around 5-15% on a worst case scenario or 15-45 conversations vs 8 hours with half the results. YMMV of course, but at least try this experiment for yourself and see the difference in your motivation.

99% of reps aren’t doing this because they don’t know how to properly execute but the strategy 100% works for the 1% that take the time. And that 1% is who makes up 80% of the revenue.

You’ve got to evolve and become the next step in human evolution or get left behind to AI SDRs or outsourced to a layoff.

Stay savage.

-Landon