Ronen R. Pessar

I Help New Leaders Thrive, Not Just Survive | When Emotions Unblock, Performance Will Unlock

We build and run your in-house outbound systems and team to outperform your competitor’s SDR teams at a fraction of the cost. Have each Rep in 40 conversations per day. Every day. 

💋I DON’T KISS AND TELL💋
[BUT MY CLIENTS DO]

💙 “I bet the house on Outbound Operators in ’25. By April, just four months in, we had already surpassed all of ’24’s SQLs. It’s like black magic.”
— Sol Broady, Head of Corp Dev @ MCI(Hired 4 SDRs instead of 34)


💙 “You smoked them. That’s over. They got the boot. You crushed them. You guys are the winners for SDR.”
— CRO, $300M+ independent digital marketing agency (600+ employees)
^ after a bake-off against another SDR firm. (Hired 1 SDR instead of 12)

Outbound Operators delivers a managed outbound system you fully own in-house. 

Built on Buckets™️, it’s the most CAC efficient pipeline engine on the planet.

🚀 WHAT YOU GET: 

ALL things SDR done for you: 
* Recruit + hire top SDRs
* RevOps (tech stack build)
* Onboarding + coaching 
* Strategic guidance

Ramping in 1–3 months, your new SDRs will consistently create more qualified pipeline at a lower CAC/TCO than hiring, training, doing tech setup/RevOps, and managing SDRs yourself.

Result: 
25–40 live decision-maker conversations per rep per day.

Our model is simple: You own it all in-house. We design it, run it, and hand you the keys. 

• One or two experienced SDRs placed in your org
• Powered by Buckets (our proven system)
• Producing pipeline = to 10-20 SDRs

Why clients choose us:

1) Faster ramp: 1-3 months to full output (vs. 9 to 12 months for typical SDRs)

2) Low CAC and TCO:Avoid $450k-$1.2M+ in wasted trial-and-error SDR teams with headcount bloat and bad strategy.

3) More output, 10x quicker, with fewer reps (PE friendly): 25 to 40 live decision-maker conversations per rep, per day.

4) We prove it before you commit. In a single 90-minute proof of concept we'll get 20+ live conversations with your buyers right before your eyes. 

The equivalent to 3-4 weeks of work for 1 SDR done in 90 minutes.

🔥 Stop lighting cash on fire with SDRs. 
🔥Plug in a system that works.
📥 DM me here on LinkedIn
🧑‍💻visit www.outboundoperators.com
📆 find time to chat: https://tinyurl.com/4h4vf35p

PS: Not ready to bring the whole kit and caboodle in-house quite yet? 

Ask about our network of fractional cold callers for hire!

Chief Executive Officer

1 - I build SDR teams to hit pipeline goals as a fractional leader (bespoke consulting)
2 - Cold Call Training (live and course)
3 - Message-market fit: 100% done-for-you email and cold call campaigns. 

**coming soon: Cold Calling Bootcamp**

Ronen 🧡 Pessar

I'm about to p*ss off my entire industry.

But someone has to say it.

Parallel dialers ruined cold calling.

Sales engagement platforms ruined cold email. 
And LI automation tools are getting shut down…

We've scaled spam, but not conversations.

The outbound "trends" we see?

→ 1 random convo every 30–65 dials
→ Numbers spam-flagged before lunch
→ Prospects annoyed before they even say “hello”
→ Multichannel “do more” (aka spam-the-TAM) as a strategy

It feels productive because the dial count is high.

But honestly, it's just expensive noise.

We ditched parallel dialing, mass emailing, and “social selling."

Our quality convos jumped from 0–2 → 25–40/day (per rep). With fewer reps. Same hours.

8–12 conversations per hour.

Cold calling isn’t dead.

But the way most teams are doing it is.

If you care about pipeline, stop scaling waste.

Build for signal, not noise.

PS: Can someone make this make sense? Plz.

JSESSIONID

linkedin.com/feed/

li_at

LinkedIn

In outbound, meetings don’t matter | Cofounder @ Outbound Operators

Scare a salesperson in 2 words ⬇️

I'll go first:

Q 4

🚨I'm hiring for a 6-figure Senior SDR 🚨

This role is a career-maker. Read on.

🥇 Company: quack.ai
📍Fully remote (USA or Canada only)  

💰 𝗖𝗼𝗺𝗽: OTE: $100,000 - 120,000
[Salary: $50k -60k | Comm: $50k - $60k, uncapped]

🫵 𝗥𝗲𝗾𝘂𝗶𝗿𝗲𝗺𝗲𝗻𝘁𝘀:
• Cold Calling only 
• Can handle 40 live convos every day
• 𝟯 𝘆𝗲𝗮𝗿𝘀 𝗼𝗳 𝗰𝗼𝗹𝗱 𝗰𝗮𝗹𝗹𝗶𝗻𝗴 𝗲𝘅𝗽𝗲𝗿𝗶𝗲𝗻𝗰𝗲 𝗿𝗲𝗾𝘂𝗶𝗿𝗲𝗱

To get the job, you'll cold call with us, live. 

If you're ready to show off your skills on the phones.
Apply here: https://lnkd.in/d8NhfmnF

PS: Know a killer cold caller? Tag a friend!

Open article: Outbound Operators - Sr. Sales Development Representative (SDR) at QuackAI by outboundoperators.recruitee.com

Outbound Operators - Sr. Sales Development Representative (SDR) at QuackAI

My favorite strategy when someone's ghosting?

Hit em with a late fee

Not sure how to go about it? I'll give you an example ⬇️ 

When I was 10 years old, I lost a tooth. 

Usually, when this would occur, I'd expect a few bucks under my pillow when I woke up the next morning. 

But this night in the early 2000's was different. 

There was no dollar when I woke up. 

Tragic? A little bit. 

What'd I do next though? I hit the tooth fairy with a quid-pro-quo: 

"If you don't give me the cash tonight, tomorrow night your fee will go up to $24.00"

A 2,400% interest rate 

The tooth fairy didn't DARE mess with me again. 

And you better believe that dollar showed up under my pillow the next night. 

Follow me for more tips like this

(2) Notifications | LinkedIn

not making cold-calls, but teaching ppl how to cold call?

hell no

not posting on LinkedIn, but teaching people how to go viral?

also hell no

not sending emails, but sharing best email practices... 

very hell no 

"Well Ronen... coaches don't play ya know"

Listen, it's not personal. The game changes. 

and you have to be in the trenches to stay relevant...

am I wrong?

Cold-calling fact:

Calling people who pick up the phone is better than calling people who don't. 

"No shit, Ronen. Thanks for the groundbreaking advice"

I'm serious though. 

If a prospect picked up once, they’ll pick up again.
You can always call them back.
You can always have another conversation.

Once that happens, everything changes:

1) You never need to “war dial” and risk pissing them off.
2) No single call really matters. Stop pushing. You’ll get another shot.
3) There’s no such thing as “the right time or day” - it’s always the right time.
4) Never leave voicemails before you have a conversation. It's a warning shot. 

Once you start calling people who actually answer the phone…
Cold-calling stops feeling cold.

LinkedIn Login, Sign in | LinkedIn

"Ronen, there's NO WAY that your reps are getting 20-35% connect rates when cold-calling"

I get one of these dm's once a week. 

So I decided to drop a value bomb on ya'll

The biggest issue with cold-calling in 2025? 

Nobody's picking up the damn phone. 

Well, at least the people you're calling aren't. 

Reps at Outbound Operators are having 40 conversations per day, with 20-35% connect rates on any given day. 

It isn't rocket science. 

But most people don't know how we're doing it. 

So I'm going to show you EXACTLY how our reps are:

• Getting a 20-35% connect rate when dialing
• Having 40 conversations per day with their ICP
• Booking more sales qualified opps than anyone else in the space

I lay it all out in a new video (step-by-step)

All you need to do:

Comment "Calls" 
(and make sure we're connected)

And I'll shoot it over 🤙

If SDRs disappeared tomorrow?

90% of companies would be gone in 12 months.

No meetings.
No pipeline.
No new revenue.

Just CEOs crying into their Series A funding.

But sure, keep setting SDRs up to fail with:

• a 2% connect rate
• a 98% failure rate
• a broken list from 2017

…and then blame them when you miss quota.

The disrespect is wild.

SDRs aren’t lucky to have a job.

You’re lucky they haven't walked out yet.


Today, I'm especially thankful for Sales Development. 

You should be too. 

Happy thanksgiving y'all! 
🦃

It should never take more than 3 days for SDRs to dial.

You don't have time to waste with non-productive weeks (or months).

• 1-2 days: on the phones
• 1 month: at 80% to quota (or better)
• 2 months: already at or exceeding quota

a typical SDR ^
At quota between months 1-2

Get outta here with that '3 weeks of onboarding' trash

On his FIRST day Gabriel Rojas already set one. 
👏 amazing first day, Gabe!!! 🎉

also... 
he had 14 connects 
on 47 dials
[30% dial to connect]

which means, 
1. learning happens very quickly
2. results happen very quickly 
   
Day one, yall.
Should look like this.

If it doesn't... https://lnkd.in/dHEq-sCj

We scaled Outbound Operators to $1M+ ARR in <18 months

If I was going to do it all over, here's what I'd do different:

1 - offer financing with buy now, pay later options for early-stage companies who are a bit more spend conscious. everyone wins. (we do this now)

2 - double down on documenting process + working with VAs... delegation is a game changer (buy back your time by Dan Martel changed my view on this)

3 - focus on balance, not ruthless, brute-force never ending hustle... my mind and body burn out VS staying energized

4 - say no to about 80% of the things I said yes to: bad clients, terms not aligned with what we do best, random marketing stuff, and so much more

Biggest thing on this list is the last one. Distraction comes in many shapes and sizes, and they get thrown at you every day. 

The more focused you can stay, the faster you'll scale. 

To infinity and beyond 🚀

Board meeting math is hilarious.

CEO: “We need more pipeline.”

CRO: “Let’s hire 12 SDRs.”

Board: “Approved.”

Three months later…

12 SDRs + 9 tools + $1.2M in burn

= 3 meetings that never showed.

Everyone: “So $4,735 per meeting is… fine, right?”

PS: What’s your favorite way to set $1.2M on fire?

In the last 2 weeks, I recorded:

→ 30 short videos
→ 10 podcast episodes w/ Ryan
→ And I’m just getting started.

Why?
Because the truth about cold calling needs a louder voice.

Its the number 1 channel for predictable, scalable revenue going into 2026.

Too many outsource to agencies that don’t know their market.

So I went on a sprint.
To build the clearest, most actionable library on outbound sales anywhere on YouTube.
Real tactics. Real calls. Real talk.

If you want to:
• Build a real outbound machine
• Have reps that can actually sell
• Or just stop burning cash on SDRs

Check out the channel.
You’ll get better with every episode.

https://lnkd.in/gSZY9Z4A

📍 YouTube: Ronen Pessar

Use a gimmicky call opener and your prospect won’t respect you.

No respect, no conversation. 
No revenue. 

Sure, gimmicks get attention, but…

They lower your status.
They destroy trust.

I use this opener. 
It works 98% of the time. 

“Hi <name>. This is Ronen Pessar. You weren’t expecting my call. It’s actually the first time I’ve reached you. I was hoping you might help me out for a brief moment.”

98% of the time they say.

“Sure.”

If you want the full script, check it out here: https://lnkd.in/gMSZtAfH

My anti to-do list 

(Specifically in sales)

1) Don't waste my time with pikers (aka tire kickers)

2) Gimmicky call openers 

I say this because I use to do it. I thought I sounded cool, but I feel like it's a 10/10 way to make yourself look like a fool.  And yes, gimmicky call openers do make me want to throw my phone out he window. 

3) Lengthy follow up emails that prospects won't read. 

Follow up emails need to be short, to the point, and easy to read. If they're long, people won't read them and you just wasted 30 mins of precious dialing time. 

4) Avoid energy vampires like the plague. 

Your energy is precious, so safeguard it. People can either suck the life out of you or give you energy. Choose to be around people that give you energy. 

5) Listen to everyone, but be careful who you take advice from

Sahil Bloom said "don't use someone else's map to navigate your reality."
Most advice is just what worked for that person. Think for yourself because more often than not, you already know the answer, you just need to do it.

Here's the EXACT voicemail playbook that turns 18.3% of my VMs to a callback (and meetings set).

[share this with your cold calling friends]


Step 1: Don’t leave voicemails.
Step 2: See Step 1.

😁

[I'll break it down in the first comment]

I will never use a parallel dialer again

I was a power user & fan for years, but that all changed for  1 consistent reason

More dials ≠ more revenue. 

Here’s why

Outbound sales is a long-term strategy, most results happen on follow up activities (not the first conversation)

Which makes sense because in outbound, the people you add to a list should be qualified, but there will be no urgency. 

Parallel/multi line dialers are a short term results tool. 

In the first 1-2 months, I will have lots of conversations and solid results. 

But then…

100% of the time that will tank and it will drop quickly. 

Because I will regularly connect with all the people who actually answer (on the first 1-5 attempts), and the prospects left on my list will NEVER answer. 

^ this is why most Nooks/Orum users will eventually have a conversation every 50 to 100 dials (1-2%) around month 3-4 of using the tool. 


TL;DR

Using a parallel dialer guarantees 1 thing…

that I call people who never answer the phone, a lot more often. 

Over 12 months, it will barely move the needle. 

Challenge me on this.

Want to book 40% more meetings in Q4?

Try this method:

Step 1: Offer your prospect $150 to take a meeting with your AE. 

Step 2: Offer your AE another $100 to take the meeting and add it into their pipeline

Step 3: Get paid $500 for a qualified meeting by your company. 

Step 4 (this is where it gets interesting): Raise $100K from angel investors, go to your local YMCA. Offer everyone $150 to pretend to be a prospect of a B2B SaaS company, and take a meeting with your AE. 

Step 5: Repeat step 2. 

Step 6: Negotiate a 10% increase in pay with your company because of how many meetings you're bringing in. 

Now, you have over $200k in cash, and can rinse and repeat until you reach your first milly. 

Then keep reinvesting profits. 

...and they say making money is hard 🙄

I'm sorry if this ruffles some feathers...

But most people that want to be successful, won't be. 

It's not because they're not motivated, it's because their actions don't match their words. 

Six figures. Fast-track to sales glory. A career with massive growth. Everyone wants that. 

But when it's time to pick up the phone?

ALL that motivation and talk disappears.

If you're not scared of 150 calls a day
If you love the idea of 40 live convos a day
If you're the type who wants a shot, to prove you're a dawg... 
(not JUST post about it...)

I’m hiring.
Offers going out asap.

[link in profile]

I have a bone to pick with sales coaches...

But not for the reason you think. 

Yes, I will admit. There are some legit coaches out there that will make you a better seller. 

BUT, the vast majority of people professing to "get you to $1M commission years"....

Have either 1) never done it themselves. Or 2) done it themselves, but worked at a company who's valuation shot up from $500M to $100B in 8 years.

They might be legit, but they were swimming downstream, working for a company that would've crushed either way. 

I think sales coaches have their place in making you a better seller. Especially if you've been a seller for years, and want to sharpen your skills. 

I do NOT think however, that SDR's should hire a sales coach. 

The only way to get better as as SDR is to DO MORE REPS. 

Have more conversation, fail more, and learn from better sellers around you. 

Don't waste your hard earned commission dollars on a coach. 

Please and thank you 💕

Hiring an agency is a horrible idea.

They will burn a whole in your wallet when you:

- don't have PMF
- don't know who your ICP is 
- don't have a solid marketing plan
- don't have your sales process locked down

Instead, hire an agency when you:

- have PMF
- have some brand awareness 
- have a sales funnel with predictable numbers

If YOU can't get your first five customers, how can you expect someone else to do it for you?

Agencies are NOT a go-to-market strategy. 

They are not a way to kindle a fire. 

But... they can be a great way to add fuel to it.   

Start the flame, then hire people to help you turn it a wildfire 🔥

PS: paying for appointments is insane. I can offer someone $250 to take a meetings, and flip that for $500, $750.. $1,000... who ever thought this was a good idea?!?

Salman Mohiuddin

Enterprise Account Executive, Marketing Cloud (Financial Services)

Helping sales pros + teams build healthy pipeline to close more deals faster | Sales Coach + Trainer @ SSA | 17 years as a quota carrier | ex-Salesforce, Asana and IBM | Interview Ace

Problem before Product. 

17 years of tech sales experience as an SDR + AE at Salesforce, IBM and Asana all as an individual contributor. There’s more 👉

Currently Founder at Salman Sales Academy.

#1 Sales Influencer in Canada 2025 (source: Favikon)

Coaching and training AEs, SDRs, BDRs + sales teams to find and close more deals.

Started as an SDR in 2006, moved to AE in 2007.

6 years at IBM
- SDR 
- SMB + MM AE
- small Enterprise AE

7 years at Salesforce
- MM AE (new logo)
- Enterprise AE

2.5 years at Asana
- Enterprise AE 

2 years at startups 
- SMB AE (new logo)
- Enterprise AE

I currently coach + train AEs, AMs, BDRs, SDRs and Sales teams on prospecting, problem enablement, discovery, demos, deal strategy and interviews.

DM me for:

- 1:1 Sales coaching 
- Sales team coaching + training for your company
- 1:1 Sales interview consults to help you land an offer
- Speaking engagements or sessions for your company
- Podcast guest 


✅ Widely recognized as a master prospector & hunter

✅ Experienced in consultative selling to C-level, Information Technology (IT), Marketing, Ops, HR and more.

✅ Sales Interview Ace - the interview playbook I've built has resulted in an 80% success rate in interviews

✅ Possess an Honors B.A., Economics

[Sales COACHING]

➡️ Problem Enablement [build confidence in truly understanding your persona and the problems your solution solves for]

➡️ Prospecting [cold email, cold calling, warm calling, objection handling]

➡️ Discovery [full 5-step discovery framework to help lead your calls with confidence and in the flow of the conversation]

➡️ Demos [full demo framework, engaging demos, justifying spend, taking control of deals, PoC/Pilot strategy, etc…]

➡️ Deal Strategy [multithreading, uncovering power, executive alignment + engagement, quantifying pain, business case, negotiation, dealing with objections throughout cycle, taking control of your deals, champion building, mutual plans, forecasting, etc...]

➡️ Interviews - I've refined my interview playbook that has help 80+ folks land offers [interviews, mock cold calls, mock discovery, mock presos, territory plans (that will wow a hiring manager)]

I've built an entire Sales playbook from prospecting to close in everything in between based on my 17 years of experience as an individual contributor in tech sales.

No fluff. All actionable sales insights and content, with real examples, that you can start using right away in your role and see immediate results.

Check out the coaching programs and testimonials here:  www.salmansales.com

or DM me. Happy to help.

Founder

Helping AEs, SDRs + Sales teams find and close more deals. 🚀 Boosting income and revenue. 

17 years of tech Sales experience, all as an individual contributor. I've been in your shoes as an SDR, Commercial, and Enterprise AE at companies like Salesforce, IBM and Asana. In the trenches. Exceeding targets. Even in economic downturns.

Documenting all of my learnings, I've built out a Sales playbook. Now I want to give back to YOU.

I teach individual contributors + Sales teams on how to sell better, exceed targets, boost income / revenue, and accelerate growth. All with actionable Sales content and insights that you and your team can start using right away. Seeing immediate results.

My AVP at Salesforce to me on last day of the fiscal year: “Thank you for not listening to me.” 😐

Let’s roll the clocks back 9 months prior.

I took over an account. Not just any, but the largest bank in the country.

My AVP - who was the AE on the account years ago - pulled me aside my first few weeks in role and said, 

“Salman, just take down the small deal in this account. We’ve sold them almost everything.” 

Not exactly what I wanted to hear from my AVP when I took over the account.

They’d already invested quite a bit with us, I get it. But I had a quota to hit. A big one.

Nobody thought we could sell them more. 

There was a small opp… and they recommended I just take it down

and move on.

……………………………………………..

Well, here’s what I did to prove them wrong 👇


BACKGROUND CHECK

- spoke to the CSM, SE, Core teams
- specialists, external partners, SI’s, etc…
- to get the lay of the land across the account


- identified a segment that had whitespace
- it was their Wealth management division


BUILT A POINT OF VIEW

- did some initial digging and discovery
- built PoV on how they may be losing rev to competiton
- because of insights not captured in real-time on digital channels


STARTED WITH THE PROBLEM

- focused on this business challenge
- uncovered a exec priority at risk because of problem
(increased market share)


MULTITHREAD

- the PoV + disco helped gain meetings with Dir/VPs
- leveraged our internal x-functional teams
- SE, CSM, Business Value, Product mgmt, etc…


VALIDATION + ALIGNMENT

- business problem, impact to the business
- uncovered metrics important to each stakeholder 
- how said metrics were being affected by problem
- impact to business if nothing actioned on


CUSTOMER’S BEST INTEREST BEFORE OURS

- shared pros and cons to each option
- options included ones that wouldn’t work in our favor
- we didn’t take one side or other, which built trust


CO-CREATED BUSINESS CASE

- with our champion
- got buy-in from each stakeholder


MUTUAL PLAN

- which was truly MUTUAL 


NO BUDGET WAS ALLOCATED

- we uncovered a problem that put a priority at risk
- they dug up budget from other areas of business

………………………………………..

The result?

Our champion achieved the 1% club, because of the impact the platform had on their segment.

I closed one of the largest deals of my career 

because our internal teams worked together to solve a big problem.

Hit almost 200% of my number (when I was told to take down the small deal)


The deal came on the last day of the fiscal year and the AVP sent me a message,

“Thank you for not listening to me”

………………………………………………………

I took my AVP’s statement at the start of the year as a challenge.

Don’t let a few words stop you from accomplishing something you believe you can do.

Helping Sales Pros Close More Deals + Crush Quota | 17 Years as an AE | ex-Salesforce, IBM + Asana | Founder, Salman Sales Academy | #1 Sales Influencer in Canada 2025

graphical user interface, text, application, chat or text message

If I started a new AE role tomorrow, I wouldn’t open the CRM.

I wouldn’t review the product slides (for now). 
I wouldn’t watch demos of features & function. 

Here’s what I would do instead in my first two weeks (and why it works) 👇


1. Find the top 3 AEs in the org
 Buy them a coffee (virtual or not) and ask:
 → “What are you doing that others aren’t?” → “What would you do differently if you had to start over?”
 I used to let ego get in the way of these convos.
 I realized: replicating what already works saves you months of trial and error.


2. Skip product enablement (for now)
 You’ll get flooded with features anyway.
 Start with problem enablement.
 Build a simple doc:
 → choose 3-5 buyer personas → list out real problems they face
→ (not capabilities, jargon or buzzwords)
→ understand how they typically tackle them today → map out the negative impact on them and business  → identify what metrics they care about/how affected 
Document how those problems show up in their world.
 This helps you speak the prospects language, when everyone else is just pitching features.

Prospects will think “this person gets me”.


3. Study your competition (and status quo) 
Not just from a deck, go deeper:
 → where they win → where they fall short → what your product does better → what problems your differentiators actually solve

👆 that last one is the most important
 You can’t stand out if you don’t know what you’re up against.


4. Master 3 customer stories
 Not surface-level. Break it down:
 → what problem were they facing → what negative impact it had (think metrics)
→ bonus points if there was a priority it put at risk → what changed after they used your product → what were the positive business outcomes

(make the champion the hero)


5. Meet your internal teams
 SDRs, SEs, CSMs, Legal, Deal Desk, Partner team, etc
 Ask them: “What can I do to make your life easier?”
 It builds trust fast, and that pays off when deals get complex.

…………………………………

Do these 5 things and you won’t just ramp up super fast 
you’ll build your internal brand.


P.S. Problem Enablement (2) is an absolute game changer… my clients ramp up SO much faster

17 years as an AE I was never taught one crucial skill.

→ how to quantify pain in deals

I was told that I should do it.  Got some high level theory on how to approach it.

Told that I needed a business case to drive deals forward.

Provided some building blocks to get there, but nothing tangible that I could use on a repeatable basis.

I tried, but couldn't crack the code.

One of the key reasons early in my career I couldn't get prospects to justify the spend and lost more deals than I won.

Until I realized something.

We're usually all measurable on something. We're accountable for certain metrics.

For salespeople it could be ACV, ARR, quota attainment, pipeline, call metrics, etc...

So that means our prospects, the personas I speak to, are likely accountable for something as well.

.....................................................................

I began applying this principle in discovery:

Once I uncover a problem and its impact.

I ask these questions in the flow of the conversation 👇 

1. what’s the KPI or metric they care about

"Linda, usually when I speak to leaders like yourself they are usually accountable for certain metrics like conversion rates or campaign ROI. If you don’t mind me asking, what KPI or metrics are most important to you?"

- they’re typically measured on something, find out what that is


2. how’s the metric being affected

"How’s that KPI or metric being affected by this problem you're facing today?"

- e.g. for a marketing leader, conversion rates could be suffering


3. do they have a target

"What's your ideal target for this KPI or metric?”

- they may have a goal to it; built trust and uncover it

(don’t create a business case on one call)


4. have they done any internal analysis 

"Not sure if you've done any sort of internal analysis, but you been able to quantify the impact to your business?"

- most cases they won’t be able to quantify the impact... still ask

……………………………………………………………

My recommendation, ask these questions to each key stakeholder in your cycle.

Each will usually have their own KPI + metrics they’re measurable on.


It will give you the foundation you need to help quantify pain

and build a compelling business case in their language... not your's.

Got a verbal from a prospect, “We’ve decided to move forward with your platform.” My response:

“Sounds great! I’ll send over an order form later today.”

I forecasted the deal for the month and told my manager the good news.

Got the internal approvals and sent it out.

One day passed. Nothing. Two days. Crickets.

Finally got a hold of them:

“When can we expect a signed order form?”

Prospect: “It’s not that simple. We’ll need to go through vendor approval. You’ll also be hearing from InfoSec to fill out some forms. Plus, we need to get in touch with legal to discuss the MSA.”

Me: “How long do you think that’ll take?”

Prospect: “I’ve seen it take as little as 6 weeks and as long as 6 months.”

Head down. I had to break the news to leadership on a deal I’d committed

👆 This situation happened more than once for me earlier in my career. Lesson learned.

................................................

Don’t assume a deal is done because a prospect gives you the thumbs up.

It’s on us to uncover their buying process, early.

You could try something that sounds like this:

You: “Linda, you’ve been with the company for 5+ years. Fair to assume you’ve been part of evaluations like this in the past?”

Prospect: “Yup.”

You: “Could you walk me through how you typically evaluate, decide, and purchase tech? What are the steps and who’s involved?”

..................................................

Or something like this, for more complex deals:

“Linda - working with customers like you, I’ve noticed that once a platform gets the green light, there’s often a vendor onboarding process

which could include InfoSec, privacy assessments, and potentially getting legal involved.

Is that something you anticipate and if so could you walk me through the process and who’s involved?”

...................................................

Get ahead of the process in your deal cycles.

It’ll save you a headache and heartache.


P.S. who’s heading over to Sales Enablement Summit in downtown Toronto today?

See you there!

Have you ever experienced something so incredible that it didn’t really hit you until after it was over?

Like way after...

That’s how I felt looking back at what happened last month in Toronto.

Our 2nd annual Sales Sprint conference. This time bigger and better.

All I can say is… next level (just check out the video below).

What I loved about it wasn’t just the top notch speakers

wasn’t just the AEs, SDRs, and Sales Leaders who attended (more than a third flew in for the event)

wasn’t just the actionable Sales content shared by some the top voices in the game

But it was the RESULTS that came out of it.

one AE messaged me , “We’ve already started implementing some of the learnings — we booked 10 meetings from our recent sales sequence!” 

another AE, “I’ve got calls I can apply the learnings to this week.”

“I put the guidance on a call today and it made a noticeable impact.”

They even intro’d myself and another speaker to their Sales Enablement lead recommending that we run training for the sales team.

Other leaders asked speakers to run sessions for their team after the sales insights shared at the conference.

THIS is why we put this on. So we can spread the knowledge, help the Sales profession level up, and allows folks to learn from each other.

(Folks came up to me saying they got a few leads from folks attending too!)

If you know me, I've always been a believer about sharing ACTIONABLE sales content based on experience in the trenches, not theory. 

So people can apply the learnings and make an impact in their day-to-day as an AE, AM, BDR or Sales leader.

..............................................................

An absolute unreal 2-days.

Highlight of the event was the Discovery and Cold Call role-play competition powered by Hyperbound's platform.

Huge shoutout to them for being a great sponsor (btw, if you haven’t checked out Hyperbound for sales enablement AI coaching, you’re missing out). Folks were raving about them at the event.

So grateful.

Let’s run it back next year!

(If you’re interested in locking in a spot for Sales Sprint ‘26, hit me up)

P.S. HUGE shoutout to MVMNT Media for capturing Sales Sprint with incredible photo and video coverage. If you’re hosting an event in the Toronto area, these folks are the real deal.

website: www.themvmntmedia.ca
Insta: @themvmntmedia

Wish someone had told me this about discovery when I stepped into my first AE role at IBM (a long time ago 🙃 )

→ “Vague, generic questions will give you vague, generic responses.”

Would've made a world of a difference if I knew this back then.

Why?

Because here’s how my discovery sounded like back then:

➤ When I uncovered some pain, asked a few questions around it, and got to impact, I’d ask:
 
“What impact is this having on your business?”

The response? Pretty generic and high level.

➤ Or when I wanted clarification on next steps after a demo, I’d ask:

 “What do next steps look like?”

The response? Pretty vague. Nothing of substance.

Then I realized… wait. My questions aren't cutting it.

Sounded like a rookie (which I was).
I needed to be more specific and more purpose behind my questions.

............................................................

Flip the script 👇 

To uncover impact, for example:

“Was talking to a few leaders in your space recently who came across this challenge, and they said it’s leading to product launch delays and missed revenue opps. Not sure if you’re seeing this, but what would you say is the ripple effect across the business?”

To uncover next steps after the a good demo, for example:

“Linda, let’s say we agreed to an investment you and your team were comfortable with, what would happen next? Could you walk me through your internal process step-by-step on how you’d get this approved and who usually gets involved?”

.........................................

When you go from asking vague, generic questions

 → to thoughtful, intentional, and specific ones

You’ll get answers with much more substance...

and it’ll help you navigate your sales cycle with much more confidence.

It starts with HOW you ask, in discovery.

Was at a conference yesterday and had 60- seconds to pitch a Sales Enablement leader I’d never spoken to before.

I had to run to a meeting and the next session was about to start.

Wanted to try to catch the leader whom I heard from someone else said she was looking for training for her team.

No time to qualify or run any discovery.

Just a shot to earn her trust (and a next step).

Here’s what 23-year-old Salman would’ve said:

“Hey Linda, heard you’re looking for sales training. I can help streamline your manual processes, help with your sales execution and increase win rates.”

😐


Here’s what 27 year-old Salman would’ve said:

“Hi Linda, how are you? What inspired you come to the conference?… that’s great. Hey I heard you’re looking for training. What are you hoping to accomplish?”

😐


Here’s what 42-year-old Salman actually said:

“Hi Linda, how are you enjoying the conference so far?”

Linda: “Going really well.”

Me: “Hey, know we got a minute before the next session. Just wanted to say I was on your website and I love how you focus on the problem you actually solve for.”

[I talked through the specific problem they solve for with no buzzwords, no product jargon]

“It’s refreshing to see that because I don’t very often.” I said


Linda: “Really appreciate that. I’ll definitely share what you just said with my internal team.”

Me: “Thanks. Ya the thing I see today with a lot of sellers is that they tend to focus more on the product vs truly understanding and articulating the problem, in the prospects language not their language.”

Linda: “You’re right…. we should connect.”

Me: “Know we have to run but let me send you a note and we can find some time, sound good?”

Linda: “Let’s do it.”

She smiled the entire convo.



Problem before product.

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