Sydney Senior

Member

Happily Ambitious

A podcast about balancing achievement, expectation, and fulfillment in the world of SaaS, Sales, and Entrepreneurship. New episodes weekly.

Co-Host

RevGenius

RevGenius is a group of revenue generating Sales, Marketing, and RevOps professionals brought together to learn, share, support, and grow with each other. You can consider us your alt work family!

Deel

SMB AE

Sell Better 

Daily Sales Show Host

Falkon

Senior Business Development Representative

Pavilion

Chili Piper

Product GTM Manager

Associate GTM Manager

Trailblazer SDR

Chili Piper is the leading inbound conversion software, used by top B2B revenue teams like Intuit, Twilio, Spotify, and Gong.

We’re on a journey to build the best company to work for and to work with while trying to make the world a better place. Our team is distributed around more than 160 cities and 35 countries around the world. Join the movement!

Sales Development Representative

Brand30

Zgraph

- Conducted sales needs analysis with new and prospective customers
- Developed solutions based on specific client needs
- Maintained existing relationships with clients through regular communication and outreach

Account Executive

Kerigan Marketing Associates, Inc.

•	Certified in Google Ads and Google Analytics
•	Managed social media accounts and Google Ads marketing accounts
•	Created monthly performance reports for clients
•	Assisted with new website development and content migration

Social Media Marketing Intern

demystifying success & happiness | co-creator of Happily Ambitious | SMB AE @ Deel | building in public | mindset + productivity | Sell Better host

Feeling lost, stressed, burned out, or unable to get off the achievement treadmill?

Want to take design a life you actually love, but don't know where to start?

One of my biggest passions is demystifying success & happiness.

I've spent a lot of my life working incredibly hard (past the point of burnout) and still not feeling satisfied by my achievements, feeling like achieving one goal only meant that the goal post had to be moved further away from the next one.

While I'm far from having figured this out, I co-host a podcast (Happily Ambitious) and a companion newsletter (The Ambitious Breakthrough) to learn from some of the best in this area and share my journey as I go.

My goal is to build in public - through my role in SaaS sales, as a podcast host, as one of the founders of a growing community, and as someone who very frequently deals with all of the stressors described above.

Matthew Roberts

Helping Strategic Finance Experts | Leading Sales Development | Growing Careers

Helping HR leaders automate, simplify and save time.

Working everyday to become the Hans Zimmer of Outbound.

Please, feel free to reach out!

2025 started with us hiring someone we were genuinely excited about.

Experienced. Respected. A Serious sales rep.

Within days of onboarding at Mosaic, it was obvious Ray Cleverly was going to make a huge impact.

And then… acquisition.

As part of the transition, we weren’t able to bring every rep across. Including Ray.

It was a tough moment for all involved.

But here’s what stood out with Ray.

There was no bitterness. No disappearing act.
 
Instead, he stayed close to me and positive about the future.

Ray made it clear that if there was ever an opportunity to run it back with the Bob Finance GTM team, he’d be all in.

Fast forward almost a year, and we did exactly that.

Now Ray is a few weeks in and already:
- Booking meetings at an incredible pace
- Creating legitimate pipeline
- Building workflows and tightening process internally and with vendors
- Making life easier for everyone around him

(Shoutout to Markus Raimondi for both sharing the numbers and shouting Ray out internally!)

I don’t have the privilege of managing Ray directly anymore, but I couldn’t be prouder watching this second chapter unfold.

Careers aren’t always linear. 

Sometimes timing gets in the way. Sometimes the door closes.

But the best reps don’t sulk — they stay ready.

Just like Ray.

And now he’s proving exactly why we were so damn excited in the first place.

Keep going, my friend. This is only getting started!

#sales #career #growth #sdrs #bdrs #salesrep

Had an incredible episode of Top Shelf: The Outbound Leadership Podcast with my now 4th favorite Cal Poly alum — Julian Alvarez, VP of Pipeline & Sales Dev at Gong.

(Still behind my wife, Ryan Ridley & Jared Wexler… but it’s close.)

As we close in on our 15th episode, I’m feeling genuinely grateful. 

The leaders who’ve taken time to share what’s actually working, not theory, but real playbooks and experience, has given me many ideas I’m already implementing in my own day to day.

A few highlights:

Nirvanna Lildharrie – leadership principles that everyone should have

Amanda Wilde – her LinkedIn playbook that is tactical and repeatable

Julian – walked through a killer Gong AI workflow their team built (we break it down in the episode below)

And that’s just scratching the surface.

We’ve got another episode coming up that’s going to be very relevant for every Sales Dev leader right now… but I’ll keep the guest and topic under wraps for the moment.

As always, please tag incredible Sales Dev leaders that Joey Williams and I should have on next.

If they’ve got superpowers the space needs to hear about, we want to spotlight them!

#podcast #sdrs #bdrs #salesdevelopment #sdrleadership #sales

When Joey Williams and I started Top Shelf: The Outbound Leadership Podcast the idea was simple...

Help SDR Leaders level up through 25 - 30 minute episodes rather than trial and error.

Over many years, there were only a few others out there with a similar mission, and none has grown faster and been more successful than SDR Leaders of EMEA, SDR Leaders of USA and SDR Leaders of APAC thanks to David Wilkins.

That's why our most recent episode was so extremely special and so much fun. 

If you're a Sales Development Leader and not following your region specific SDR Leaders of X page, listening to the Top Shelf podcast, or attending Funnel 26, you're doing yourself a massive disservice. 

This role is tough, often under resourced, and sometimes straight up disrespected. 

Don't make it tougher on yourself; find others that are networking, sharing best practices, teaching you skills that take years to learn and supporting one another throughout.

When any SDR Leader wins, we all win.

Check the episode out in the comments below and tag the next super hero SDR Leader we should connect with in the comments below!

p.s. shout out to Funnel 26, Hilton & Liquid Death for unknowingly sponsoring this episode...

#podcast #sdrs #bdrs #salesdevelopment #sdrleaders #learning #growth #community

Anyone have a killer podcast agency or solo operator they swear by?

Joey Williams and I are looking for someone who can:

- Edit the full episode
- Get video live on YouTube
- Cut 2–3 strong clips per episode for LinkedIn

Starting at 2 episodes per month and scaling to 4 very soon.

If you’ve got someone great (or are someone great) flood our DMs, PLEASE!

#podcast #job #editing #hiring

Almost 9 years ago, a good friend Paul Yoon connected me with a guy building a tiny website where founders shared their startup stories.

Last week he sold it to HubSpot.

Which is why I wanted to give a shout out (even if a week late) to Pat Walls on the successful sale of Starter Story!

At the time, Pat was building a simple website where founders shared how they started their companies. 

He asked if we’d be open to sharing the story behind PEAR Cards, and we were happy to be one of the early ones featured.

Fast forward to last week… Pat's story is all over the internet.

But what makes this story cool isn’t just the outcome.

It’s the process.

For years Pat talked about something he believed deeply in:

The compounding effect of consistent work.

A few hours of focused work every day.

Deep work outside the 9-5.

Building something slowly, year after year.

So many people talk about this idea.

Very few people actually stick with it long enough for it to work.

Pat did.

I actually saw it firsthand when we met up in Vietnam in 2019.

He was living abroad, working out of a tiny room, grinding on Starter Story every day.

Meanwhile, I was about to restart my tech career and join Chili Piper, which kicked off a great run since with CP, Mosaic.tech, and now HiBob.

It was incredibly inspiring seeing someone quietly doing the work long before the headlines.

Pat earned this one.

Huge congrats, my friend!

And for anyone thinking about starting something or betting on yourself…

Just start.

The compounding effect is real.

#growth #founder #acquisition #sale #grind #hustle

taplio

The Battle

Sydney Senior

Matthew Roberts

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taplio

The Battle

Sydney Senior

Matthew Roberts

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Matthew Roberts's LinkedIn Performance

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Performance ScoreMatthew Roberts's LinkedIn Performance