Hamish Stephenson 🦘

Award winning GTM Recruiting Expert | CEO @ Selr.io

Ex-President's Club seller, turned Entrepreneur. Since becoming an Entrepreneur, I have been hand picked by Linkedin as one of their Sales Insiders, been included in LDN's 40 under 40 and been a key note on a lot of high end sales podcasts. Sales is my life. I am a sales expert and startup advisor with over 10 years of experience in SaaS, sales, GTM and recruitment. As the Founder and CEO of Selr.io, I help companies build their sales and revenue functions, and retain their staff.I am also a strategic advisor for several tech startups, where I share my insights and expertise on product-market fit, customer acquisition, and growth. I am passionate about solving problems, creating value, and empowering others. I am always open to connecting with like-minded professionals and learning new things. Some of my interests include skiing, NFL, music and rugby. Talk to me about Avicii, Sydney Roosters 2013 Premiership win or Blink-182 and you'll have my ear all day.

Strategic Advisor

What is Selr.io?

Selr.io is a sales enablement and recruiting company, providing expert sales training, sales recruiting and advisory. We believe in upskilling individuals from all walks of life, preparing them and partnering with them in their career in SaaS sales.

Why is Selr.io different?

Many try to overcomplicate sales. We simplify it and make it relatable. Selr.io has built their program based on emotive selling. Since like people, all sales processes are different.

How can Selr.io help companies?

We can help you recruit, train and build a GTM plan and/or sales function. We can coach/train your sales team in prospecting, discovery and deal strategy. We are ex SaaS sales people, turned sales recruiters and trainers. 

How can Selr.io help individuals?

We can help you get into SaaS sales and develop your skills. We can help you if you're struggling with prospecting, sales process and/or closing. We can train, coach, recruit and mentor you to become an elite seller.

Alan Ruchtein

CEOs: Broken pipeline & poor performer sales reps? I fix both for you in <60 days. You’ll hate how fast it works. | Modern Seller Program Founder

Your ability to book meetings, negotiate, and close deals with potential clients will determine how far you’ll thrive as a sales rep and leader.

This will allow you to:

📈 Build a career
📈 Hit your quotas
📈 Get recognition
📈 Get a promotion
📈 Get better offers
📈 Land sponsorships

However, booking meetings and closing deals it’s harder than ever:

❌ Prospects don’t return your calls
❌ Prospects don’t stop ghosting you
❌ Prospects don’t answer your emails
❌ Prospects don’t trust you as a seller
❌ Prospects don’t believe in your offer 
❌ Prospects don’t accept your LinkedIn Invite

All of these makes you feel miserable

You feel your manager’s pressure on your shoulder

And you start thinking that sales might not be for you.

Do you relate with this? Because I do - I’ve been there

This happens because the “old way” of doing sales doesn’t work anymore.

Sending 1000s of generic emails and praying they get back to you will kill your sales career.

Now, imagine having a proven system that allows you to systematically:

✅ Book more meetings
✅ Handle all the objections
✅ Move deals through the pipe
✅ Close higher tickets in less time
✅ Run discovery and demo calls like a pro

And, hitting your sales quota.

Wouldn't this be the scenario you would like to be in?

The good news - I can help you get there with:

➝ My weekly Newsletter with actionable sales tactics
➝ My daily sales practical examples in my Content
➝ My sales personalized program
➝ My 1-on-1 Coaching Sessions
➝ My team Coaching Sessions

Now, how serious are you about building your Sales Career?

Let's make it happen.

👉🏼 Shoot me a DM, or head over to my Featured section.

I'll see you at the top!

Founder

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A weekly email focused on the evolution of Startups, Sales, and SaaS. A fun and human voice. Everything you need to know in less than 5 minutes. No BS.

AI Sales Mastery Playbook (2025 Edition)

EDIT: GET IT HERE (too many comments):  https://lnkd.in/dWiMApV8
EDIT: GET IT HERE (too many comments): https://lnkd.in/dWiMApV8
EDIT: GET IT HERE (too many comments): https://lnkd.in/dWiMApV8
EDIT: GET IT HERE (too many comments): https://lnkd.in/dWiMApV8

Every framework a modern sales pro needs in one cheatsheet:

Save this post and bookmark it before it disappears from your feed

Here’s what you’ll find inside →

-Research & ICP Definition Framework
-Prospecting Intelligence System
-Personalization & Messaging Strategy
-Cold Email + Cold Calling Playbooks
-Discovery & Qualification Framework
-Objection Handling Library
-ROI Storytelling & Proposal Builder
-Negotiation & Closing Scripts
-Multi-Threading & Deal Review Systems
-AI Tools, Automation & Performance Stack

Plus 10+ more frameworks to help you sell sharper, close faster, and scale consistently in 2025 and 2026

If you want to get the full high-resolution cheatsheet in PDF format, let me know below and I’ll share it with you

If you’re looking to train your team to perform like elite sellers and consistently hit quota, DM me “2026” and let’s talk. (2 last spots to work with me until the end of the year)

8 AI Prompts That Actually Book Meetings (Cold Email Advanced Edition)

(+ the exact wording I use to land 79+ meetings/month)

☑ ICP Research Prompt

“Act as a sales analyst. Analyse CTOs in B2B SaaS (100–500 employees). Summarise their top 5 priorities, daily pains, and buying triggers in less than 200 words.”

☑ Personalization Hook Prompt

“For this LinkedIn profile [link], draft 3 icebreakers. Keep under 20 words, avoid flattery, tie to their recent activity. Avoid jargon, buzzwords or being salesy.”

☑ Problem Hypothesis Prompt

 “Write 3 pain-point hypotheses for VPs of Sales in SaaS who missed quota last quarter. Keep each under 15 words. Make them relevant and give me a 1 line “Why it matters” for me to understand your POV”

☑ Objection Handler Prompt

 “Give me 3 tactical responses to ‘too expensive’ objection for SaaS buyers in X industry for Y role/title that are willing to buy [my solution]. Make it consultative, not defensive. Each reply must be under 25 words.”

☑ CTA Prompt

"Generate 3 high-converting CTAs for a SaaS demo request email. Each CTA must be under 12 words, avoid pushy sales language, and emphasize clear, outcome-driven value that motivates action without pressure. Prioritize clarity, psychological pull, and alignment with a business decision-maker mindset."

☑ Follow-up Prompt

"Craft a compelling two-sentence follow-up email for a prospect who opened but did not reply to my initial message [insert message 1]. Provide fresh value by weaving in a single new, research-backed insight or market trend that sparks curiosity and relevance, while keeping the tone consultative rather than transactional."

☑ Case Study Builder Prompt

"Transform the following customer testimonial into a concise, two-line cold email case study. Highlight quantifiable ROI, specific numbers, and credible impact in a way that feels authoritative yet humble—avoiding overt self-promotion while ensuring the results command attention and trust."

☑ Multi-Thread Prompt

"Identify 3 alternative stakeholders to approach if a VP of Sales does not respond. For each contact, justify their relevance by explaining their role in the decision-making ecosystem, their potential influence on the buying process, and how they could shape or accelerate a purchasing conversation."

♻️ Repost this so more people stop using GPT like an intern

Your SDRs shouldn’t exist.
At least not the way you make them operate.
This is THE way to do it:

Spray-and-pray sequences.
No signal, no strategy. Just spam.

That’s exactly where one VP of Sales was stuck.

Inbound was “OKEY”.
Outbound? Wasting time and budget.

We fixed their system using Alta | AI Revenue Workforce, and built a 24/7 GTM system that actually talks to itself.

2 AI SDR agents:

𝗞𝗮𝘁𝗶𝗲 (𝗼𝘂𝘁𝗯𝗼𝘂𝗻𝗱) tracks live buying signals, builds personalized lists, runs targeted outreach.

𝗔𝗹𝗲𝘅 (𝗜𝗻𝗯𝗼𝘂𝗻𝗱) qualifies and books inbound leads instantly. No delays. No human drop-off.

But the real magic? They work as a system. Check 2 strategies we applied:

1. 𝗜𝗻𝗯𝗼𝘂𝗻𝗱 𝗳𝘂𝗲𝗹𝘀 𝗼𝘂𝘁𝗯𝗼𝘂𝗻𝗱

Inbound spiked from mid-market fintech teams. Alex flagged it.

Katie built a list of 30 lookalikes: 

→ Same tech stack
→ Similar hiring trends
→ Matching ICP

Campaign launched: “We’ve been helping fintech teams tackling [pain] by doing [action]. Sound familiar?”

Follow-up: “Still relevant?” + 1-line value hook

Result: 4 meetings in 2 days. 2 came from auto follow-ups. No human touch.

2. 𝗢𝘂𝘁𝗯𝗼𝘂𝗻𝗱 𝗿𝗲𝗮𝗰𝘁𝗶𝘃𝗮𝘁𝗲𝘀 𝗶𝗻𝗯𝗼𝘂𝗻𝗱

Alex qualified an inbound VP. Timing was off.

Katie set a smart trigger: “Re-engage if they post a new SDR role."

Three weeks later, it fired. 

Message: “Saw you're hiring SDRs, still thinking about pipeline coverage?”

13-minute reply.
Meeting booked.
Deal closed 22 days later.

Inbound and outbound aren't different departments.

They're one system, when you build it right.

If your sales motion still feels like ping-pong, it’s time to play relay.

What are you waiting to implement AI at scale like I do with my clients using Alta | AI Revenue Workforce?

These are my 7 go-to frameworks that actually get replies:

AI won’t book meetings for you, but it’ll make sure you never run out of ways to start one

1: Pain Point + Case Study

Start with what actually hurts, back it up with proof, and end with curiosity.

2: Lead Magnet Strategy

Give value first, earn attention before you ask for time.

3: Trigger → Question → Value → CTA

Anchor to something real, ask something sharp, connect it fast.

4: Trigger → Agitation → Social Proof → CTA

Show them the pain, show them who fixed it, invite the same.

5: Competitor → Differentiation

Don’t bash but compare. Make improvement the obvious next step.

6: Bold Observation → Soft CTA

Start with truth. End with permission. It feels human because it is.

7:  External Resource Bump

Follow up with something useful. Stay relevant without chasing.

Every one of these has been tested and every one converts.

Comment “Frameworks” and I’ll DM you the Notion Library of email templates.

👉 Follow Alan Ruchtein for more outbound strategies

AI will replace you if you keep using it like Google. Here’s how to use it like a top 1% seller

8 ready-to-go use cases:

1️⃣ Prep with Purpose

Use GPT or Perplexity to build a 3-minute intel brief before every call.

Prompt: “Summarize [Company Name]’s recent goals, funding, and biggest growth blockers and translate it into 3 talking points I can use to sound like an insider.”

You’ll open calls like someone who’s already on their team, not a stranger with a script.

2️⃣ Ask Smarter Questions

Prompt AI to generate layered discovery questions that surface budget, risk, and urgency.

Prompt: “Write 5 discovery questions to uncover timing, internal risk, and cost of inaction for a CRO.”

Example: “What happens if this project gets delayed another quarter?”

This turns curiosity into control, you lead the conversation, not the buyer.

3️⃣ Connect Features to KPIs

Drop your demo script into GPT.

Prompt: “For each feature, link it to measurable outcomes, CAC, sales velocity, or cost per rep.” 

Stop demoing features. Start selling business impact.

4️⃣ Handle Objections Before They Happen

Use Claude to pre-empt resistance.

Prompt: “List 5 objections a CRO would raise about [your product] and reframe each using ROI or opportunity cost.”

Example: “It’s too expensive” → “It’s more expensive not to fix this.” 
Anticipate the objection, then weaponize it in your favor.

5️⃣ Build Tiered Proposals

Ask GPT to structure Core vs. Premium options.

Prompt: “Create two pricing options: one focused on essentials, one on maximizing ROI and minimizing risk.”

Result: Buyers stop negotiating on price, they start choosing value.

6️⃣ Create Recaps That Sell for You

Feed your call transcript into GPT.

Prompt: “Summarize this call into: 1) key pains, 2) desired outcomes, 3) ROI language.”

Then paste it in your follow-up email. You’re not just recapping, you’re reinforcing the business case.

7️⃣ Coach Yourself with AI

Upload recordings into Momentum, Spiky, or GPT.

Prompt: “Evaluate my tone, pacing, question quality, and objection handling. What would a top rep do differently?”

AI becomes your personal sales coach , available 24/7.

8️⃣ Track Wins & Patterns

Feed GPT your notes or transcripts.

Prompt: “Compare my last 10 won vs. lost deals, identify patterns in tone, language, and question types.”

Double down on what builds trust. Cut what kills deals.

If you want to plug this AI sales workflow into your team, and train your reps to sell like top performers , DM me “SYSTEM.” 

I’ll show you how to make AI your unfair sales advantage

Cold email isn’t dead. You treat it like it’s 2018.

3 problems I see every day (and how to solve them):

 • Prospecting = copy-paste LinkedIn bios
 • Emails = walls of text + zero POV
 • Follow-ups = “just checking in”

Here’s how I fix it with AI (20 moves you can copy today):

1: Prospecting & Research

Pull live triggers (funding, hiring, launches) in seconds with @Perplexity
Summarize top 3 pain points per persona
Flip competitor case studies into proof points

2: Email Creation

Generate 5 subject lines under 5 words
Convert LinkedIn posts into personalized openers
Shrink case studies to <25 words with ROI metric
Swap “30 min call?” with micro-yes CTAs (slide / quick reply)

3: Follow-Ups & Objections

Auto-generate 40-word bump emails
Reframe “No budget” with COI (cost of inaction)
Turn an article into a 2-line nurture follow-up

4: Testing & Optimization

Create 3 rewrites for A/B tests
Cut every email to <67 words
Rewrite tone for CFO vs CMO

5: Scaling & Sequences

Build 3-step Intro → Proof → Bump flows
Repurpose as LinkedIn DMs
Save winning prompts into a template library

Pro tip: Create your Buyer persona matrix + cold email sequence for FREE with this Custom AI GPT - https://lnkd.in/dSiceii6

Why this matters:

AI doesn’t just “write faster.”

It gives you a repeatable system for research → message → follow-up → scale.

Instead of guessing → you run a playbook that compounds every week.

If your outbound team is still stuck at <3% reply rates, you don’t need another template, you need a system.

That’s what I build for clients:

→ ICP research automated with AI triggers
→ Sequences that sound like top reps (not robots)
→ Playbooks that compound results week after week
→ Trainings that help your team to perform like elite sellers

If you want me to help you map this system with your sales team, DM me to see if we’re a fit to working together.

Only reps who adapt to outbound will own the next decade:

Outbound is evolving

Evolution adds new layers

Reinventions delete what no longer works

Outbound didn’t die, attention did

Buyers didn’t stop responding because they hate sales or being sold

They stopped because you didn’t evolve as fast as they did

-Cold calls turned into “silence unknown callers.”
-Cold emails turned into “promotions tab.”
-AI-generated spam finished the job.

The problem isn’t automation. It’s that you are not original anymore

Outbound isn’t dead. It’s just going AI-native

In 2026, the best reps won’t send more messages; they'll build systems that learn from every rejection, trigger, and win

Every AI Sales workflow I built last year taught me one thing: If you can’t translate your offer into pure relevance to your prospect, your automation just scales the noise

And your “beautiful email” is just BS and s*cks

I’ve sent and analyzed +50,000 cold emails. Reply rates dropped +47% when context and relevance was missing

AI didn’t “replace” sellers. It equipped elite ones with a system ten times faster, and harder to ignore

What’s replacing sellers?

-Outbound that thinks
-Outbound that listens before it speaks
-Outbound that runs on signal, not spam

That’s the reboot

Sincerely, Alan Ruchtein

Leave your radical hard opinion below:

2 emails, 1 meeting booked in 10 minutes.
The Email Forward Strategy (explained below):

Most cold emails get ignored.

But there’s a play that flips the script — and books meetings fast.

I call it The Forward Strategy.

Here’s how it works:

You’re targeting a mid-market SaaS org. Their CRO just posted on LinkedIn about missing revenue targets.

In the comments: pipeline quality comes up.

𝗦𝘁𝗲𝗽 1: 𝗘𝗺𝗮𝗶𝗹 𝘁𝗵𝗲 𝗖𝗥𝗢

“Saw your post on rev targets. Teams in your space are tightening up pipeline quality by doing X, might be worth a look.”

You’re not expecting a reply.
You’re planting a signal.

𝗦𝘁𝗲𝗽 2: 𝗙𝗼𝗿𝘄𝗮𝗿𝗱 𝗶𝘁 𝘁𝗼 𝘁𝗵𝗲 𝗩𝗣 𝗼𝗳 𝗦𝗮𝗹𝗲𝘀

With one sentence on top: “Saw this from [CRO Name], figured you might want eyes on it.”

Why it works:

→ It looks internal. Like the CRO passed it down.
→ It feels relevant. No pitch, just intel.
→ It uses social proof sideways. Exec is the signal. VP takes action.

It doesn’t feel like outreach.
It feels like context.

Here’s how to run it:

Find a CRO public trigger tied to a pain you solve. 
Send them a cold email with a sharp POV.
Forward it to their VP with that one-line intro.

No faking. No fluff.
Just smarter sequencing.

It’s not mass automation.
It’s surgical outbound.

Want to make it land? I use FullEnrich to get all the right emails and data.

Because even the best play flops if you’re emailing the wrong (or no) person.

#fullenrichpartner

Brand partnership • CEOs: Broken pipeline & poor performer sales reps? I fix both for you in <60 days. You’ll hate how fast it works. | Modern Seller Program Founder

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Alan Ruchtein

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