RVP, Sales @ Bullhorn - I talk about creating systems for sellers to scale your impact, not your hours

3 years ago, I was drowning...

As an RVP at a fast-growing tech company, my life had become an endless stream of:

• "Urgent" emails
• Back-to-back meetings
• And constant fire-fighting

Waking up early and working late into the night.

My phone was always buzzing with notifications.

To make matters worse, it was taking a toll on my family.

The breaking point:

Missing my son's jujitsu belt test.

Something I'd promised I wouldn't do.

That night, seeing the disappointment in his eyes, I knew something had to change.

I spent the next year obsessively learning, developing & testing different productivity systems that would allow me to:

• Still perform at a high level
• Stop feeling perpetually overwhelmed
• End working nights/weekends just to keep up

I started creating what I called "mini-systems"

Small changes that had a compounding effect.

What began as a quest to regain control of my calendar...

Evolved into an operating system that helped me recover 10+ hours every week.

More importantly, spend more time w/ family. 

I've started documenting my learnings & "mini-systems" and now share them with others through my content and weekly newsletter The Systematic Sales Leader.

My goal is to help as many sales leaders as possible avoid the same burnout I and so many others experience through tested and proven systems.

If you're curious to learn more, check my "featured section" for a few free resources.

The biggest lie in sales:

(That most believe but shouldn't)

You need to be extremely outgoing to have success.

I've worked with 100's of sellers.

The top 20% share the following:

They listen more than they speak
They do their homework before every call
They follow up with precision, not persistence
They ask better questions than they pitch features
They build trust through consistency, not charisma

Your personality type doesn't determine your quota attainment.

Your preparation and process do.

Keith Weightman

Talks about #saas, #sales, #salestips, #prospecting, and #salesdevelopment

How many of these are you doing, and what's 1 you'll start using this week?

How to Build 3-4 stakeholder relationships

After years of being LinkedIn friends, finally met Samantha McKenna in person the other day.

True to form, she brought her signature SMYKM (Show Me You Know Me) energy by picking a spot called Best Buns. If that’s not personalization, I don’t know what is.

It was one of those rare moments when someone is exactly who you thought they’d be, just better in person. 

We’re both in VA, so looking forward to the next one.

Fun fact about me: I've never owned a dog.

But I draw them pretty regularly, because...

1. I like to draw, and they're easier than humans
   
2. Their owners seem to enjoy my average sketches 

3. They make good gifts, and I'm terrible at shopping

So if you're looking for a hand-drawn sketch of your pet as a holiday gift, shoot me a DM. 

P.S. Also works if you're terrible at shopping and need something for the person who has everything except a mediocre drawing of their pet.

What’s your favorite holiday movie - BUT you can only comment a quote from the movie not the title. I’ll go first…

“Sh*tter was full”

Think about your last great purchase decision.

Did the salesperson wow you with their pitch?

Or did they ask the right questions?

Did they dominate the conversation?

Or did they make space for you to think out loud?

The sellers who consistently win deals understand:

Customers don't buy from people who talk the most.

They buy from people who understand them best.

And understanding requires:

• Listening without planning your next sentence
• Asking follow-up questions instead of moving to features
• Creating space for them to articulate their actual needs
• Observing what they're not saying

The sales profession doesn't need more "smooth" talkers.

It needs more thinkers.

Agree or disagree?

"Just read more books" is the worst advice I've ever received...

I'd spend months forcing myself through sales and leadership books. 

Highlighting passages that seemed important.

Dog-earing pages I swore I'd revisit.

Feeling productive.

The problem?

Anything I learned evaporated from my small pea brain as soon as I closed a book.

"Just read more books" does nothing if you can't actually remember what you read.

The advice isn't wrong. The execution is.

So I built a mini-system to help solve my own problem. 

If you care to check it out, tomorrow's newsletter breaks it down:

• Capture insights from physical books in 10 seconds
• Remember what I read using science-backed techniques 
• Access every book I've ever read in my daily workflow 
  
𝗕𝗢𝗡𝗨𝗦: I just finished reading Nate Nasralla's new book "Brief & Brilliant" (coming out 11/20, and it's a must read). I'm including my complete highlights so you can see this system in action.

Get tomorrow's issue in your inbox at 10am sharp here: https://lnkd.in/ewB99KND

𝘗.𝘚. 𝘛𝘩𝘦 𝘪𝘯𝘵𝘦𝘨𝘳𝘢𝘵𝘪𝘰𝘯 𝘯𝘰𝘳𝘮𝘢𝘭𝘭𝘺 𝘶𝘱𝘥𝘢𝘵𝘦𝘴 𝘵𝘩𝘦 𝘯𝘰𝘵𝘦𝘴 𝘸𝘪𝘵𝘩 𝘵𝘩𝘦 𝘣𝘰𝘰𝘬 𝘤𝘰𝘷𝘦𝘳. 𝘚𝘪𝘯𝘤𝘦 𝘵𝘩𝘦 𝘣𝘰𝘰𝘬 𝘪𝘴𝘯'𝘵 𝘳𝘦𝘭𝘦𝘢𝘴𝘦𝘥 𝘺𝘦𝘵, 𝘐 𝘮𝘢𝘥𝘦 𝘮𝘺 𝘰𝘸𝘯, 𝘧𝘦𝘢𝘵𝘶𝘳𝘪𝘯𝘨 𝘵𝘩𝘦 𝘢𝘶𝘵𝘩𝘰𝘳 𝘢𝘯𝘥 𝘵𝘩𝘦 𝘮𝘢𝘯 𝘴𝘺𝘯𝘰𝘯𝘺𝘮𝘰𝘶𝘴 𝘸𝘪𝘵𝘩 "𝘣𝘶𝘴𝘪𝘯𝘦𝘴𝘴 𝘤𝘢𝘴𝘦."

I've spent 10 years leading AE & AM teams and managing $60M+ territories. Here are 5 lessons I wish I had known before I started:

1. 𝗧𝗶𝗺𝗲 𝗶𝘀 𝗮 𝗪𝗲𝗮𝗽𝗼𝗻, 𝗡𝗼𝘁 𝗮 𝗥𝗲𝘀𝗼𝘂𝗿𝗰𝗲

Most sellers think more time = more deals.
So they:

• Join every call
• Take every meeting
• Chase every opportunity

I've seen $100k deals lost to $100 distractions.

The best sellers use time as a weapon:

They cut what doesn't matter
To double down on what does

A focused hour beats a busy day.

-----

2. 𝗗𝗲𝗲𝗽 𝗪𝗼𝗿𝗸 𝗕𝗲𝗮𝘁𝘀 𝗗𝗲𝗲𝗽 𝗛𝗼𝘂𝗿𝘀

I used to pride myself on 60+ hour weeks.

Then I discovered something counterintuitive:

My best quarters came when I worked less but worked smarter.

Implemented a Deep Work System:

• 3x strategic work completion
• 23% fewer internal meetings
• Higher win rates

-----

3. 𝗧𝗵𝗲 𝗟𝗼𝗻𝗲𝗹𝘆 𝗟𝗲𝗮𝗱𝗲𝗿 𝗧𝗿𝗮𝗽

New sales leaders think they need to:

• Solve every problem
• Have every answer
• Fight every battle

It's exhausting. It's isolating.
And it's completely unnecessary.

Great leaders build network, not silos:

• Build support system across teams
• Lean on peer leaders for advice
• Share wins and losses openly

Your success scales as soon as you stop trying to be the hero of every story.

-----

4. 𝗧𝗵𝗲 𝗗𝗲𝗮𝘁𝗵 𝗼𝗳 "𝗔𝗹𝘄𝗮𝘆𝘀 𝗢𝗻"

Browser tab overwhelm
Calendar Tetris anxiety
Notification hell

I built a Focus System that:

• Cut notifications by 67%
• Reduced email time by 73%
• Created actual weekend freedom

Your devices work for you.
Not the other way around.

-----

5. 𝗦𝘆𝘀𝘁𝗲𝗺𝘀 𝗕𝗲𝗮𝘁 𝗛𝘂𝘀𝘁𝗹𝗲

"Just work harder" is lazy advice.

Top performers stack "mini-systems" to scale their impact, not their hours.

-----

What others would you add?

P.S. Here's where I share more about my favorite 'mini-systems' https://lnkd.in/ewB99KND

What's a current sales tactic, strategy, or trend that you're 100% sure people will cringe at in 10 years? What's gonna be the next "oh god we actually did that" moment?

4 mistakes that average sellers make during discovery:

1. Rushing past the problem phase to present solutions before the client fully articulates their pain points.
   
2. Asking vague questions ("Is this difficult?") instead of specific ones ("When your CRO requests pipeline data before the board meeting, what specific manual steps do your sales ops team handle that take the most time?")
   
3. Missing emotional signals that indicate strong problem areas, like frustration, worry, or stress, in a client's language.
   
4. Failing to connect problems to specific capabilities in your solution.

What others would you add?

Most job seekers are buried on LinkedIn. And they're doing it to themselves.

Here's how:

Their typical approach:

Search openings
Apply to 200+ jobs
Get about 3 responses

Zero posts
Zero comments
Zero engagement

Meanwhile, the people actually landing roles?

They're doing the opposite.

They're visible before they need to be:

Posting about their industry
Sharing what they're learning
Commenting on other people's content
Building relationships, not just sending applications

If you're job hunting on LinkedIn like it's Indeed, you're already underground.

The people winning?

They made sure everyone knew their name before they ever needed to ask for help.

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