Rich Adams

Director, Enablement Programs + Strategy 

Workiva

Helping build a culture of sales excellence & coaching at Workiva as a member of the sales enablement organization.

Lead Field Coach - Americas 

Rich Adams Sales Advisors

🌟 Freelance Sales Strategy & Enablement Expert 🚀 | 15+ Years of Success in SaaS Sales & GTM Strategy | Helping Sales Teams Excel and Delight Customers 

Are you seeking a seasoned Sales Strategy & Enablement Expert to elevate your sales team's performance and deliver exceptional customer experiences? Look no further!

🔹 About Me:
With over 15 years of experience in SaaS Sales and Go-to-Market (GTM) strategy and execution, I specialize in helping organizations define, build, and execute winning sales enablement strategies. My mission is to empower sales teams to stand out in the market and exceed customer expectations.

🔹 What I Offer:
🚀 Rich expertise in crafting and implementing effective sales & and enablement strategies
🛠️ Proven track record in GTM strategy and execution
💼 Fractional enablement leadership + execution 
💡 Modernizing sales processes and team enablement
🌐 Consulting, project-based, and fractional roles


I'm open to freelance consulting, project-based work, and fractional roles to support organizations in modernizing their sales processes and enhancing team performance. Whether you're looking to fine-tune your sales strategy, boost your sales team's effectiveness, or revamp your GTM approach, I'm here to help.

📬 Feel free to reach out for a chat! Direct message me to explore how we can work together to achieve your sales and customer experience goals. Your success is my priority!

Fractional Sales Enablement Leader | Coach | Consultant | Advisor | SME

Pavilion

Associate - Member

BombBomb

People buy from people. Humanize your sales motion using video messaging and build relationships faster, and close more business. 

Building the strategic account expansion & enablement strategy to help more BombBomb customers expand their use of video messaging to build better relationships,  drive more sales, improve productivity, and humanize their business.

Strategic Accounts, Manager 

Bravado

I fill critical enablement needs to help small businesses successfully build & onboard fractional sales teams through Bravado Flex.

- Built an end-to-end enablement strategy & sales playbook in partnership with Head of Sales to successfully onboard a flex sales team in less than 2 weeks
- Setup sales tools like Apollo and optimize for outbound sales motions + hit key sales metrics 
- Build outbound sales messaging, talk tracks, cold email templates, and end-to-end workflows 
- Facilitate live coaching + and training sessions for flex sales teams 
- Advise flex sales leaders & co-founders how to accelerate ramp time for flex sales reps

Fractional Sales Enablement Expert 

RevShoppe

Rich overhauled the enablement pillar for RevShoppe, and implemented a new enablement methodology across RevShoppe programs that will drive more value for clients and increase overall sales engagement adoption. 


‍RevShoppe is transforming sales engagement through executive strategy and tactical workflows. By optimizing operations, messaging, and enablement, our operating models empower executives to scale their go-to-market strategy and deliver an unrivaled buyer experience.

Zoom Video Communications

The front-line sales manager is the force multiplier of a sales organization. Unfortunately, most revenue teams forget about enabling their most important player. 

Following the “Zoom boom” I had the chance to build Zoom's first sales manager excellence program with the help of an amazing team that was designed to help sales managers excel in their roles, elevate their team's performance, and create a healthy and winning sales culture. 

I had the chance to train hundreds of new and existing managers on cutting-edge coaching strategies, new tools, and leadership best practices.

Sales Enablement Manager, Manager Execution 

After successfully building the training & enablement strategy across Zoom's sales tech stack that was critical for a successful IPO, I got the opportunity to build a specialized team focused on driving strategy, enablement, and innovation of the global sales technology stack. 

We built dynamic sales playbooks, influenced how and when sales tools were used through the sales and buyer journey, drove adoption strategies,  and continued to push the limits on how technology & AI can empower the revenue organization at Zoom. 

We helped the global team accelerate & build pipeline, increase win rates, add predictability to revenue, and enhance Zoom's pipeline management & forecasting process through better use of tools.

Creating the scalability of systems and tools enabled Zoom to scale ($100m - $4B ARR) at a rapid rate during the pandemic where speed and agility were critical.

Core Sales Tech Stack 

✔️ Outreach  
✔️ LinkedIn Sales Navigator 
✔️ Chorus.ai
✔️ Clari 
✔️ People.ai 
✔️ GURU 
✔️ Workramp 
✔️ Zoominfo

Manager, Sales Tools Strategy (RevOps)

I was hired to join the nimble sales enablement organization that would end up training & onboarding the core sales team that took Zoom through one of the most successful SaaS IPOs. 

My focus was to maximize ROI and adoption of the sales tech stack through creative training and mapping key sales tools to critical stages of the sales and buyer journeys. 

I created hundreds of training modules, videos, and tutorials, and led 100+ live and virtual training workshops focused on driving sales velocity through better use of sales tools. 

This function was critical in scaling Zoom through a successful IPO and setting the table for hypergrowth.

Sales Tools Trainer (enablement manager)

Conga

Conga acquired May 2020 by Apptus 

Promoted to lead and build out Major Account Sales  & Account Management Team, focused on growing strategic accounts in North America (1,000-5,000 employees), accounting for 50% total MRR bookings eventually leading to successful exit.

Manager, Major Account Sales

Launched Conga's first Global Account Management team focused maximizing customer value, and  driving upsell and cross-sell of Conga's full suite of intelligent document automation products to global customer base. Was instrumental in building the install base sales model that fueled record 200% YoY growth,

Manager, Account Management

Ambassador - Referral Marketing Software

Ambassador acquired by West Corp Oct 2018

Successfully built out Ambassador's Denver based enterprise sales office.  In first 90 days, developed a  new business acquisition & account based sales strategy that consisted of hiring and training  an outbound SDR team that drove a 40% increase in outbound sales opportunities across the global sales pipeline, fueling the rapid adoption of Ambassadors platform across B2C and B2B companies in less than 12 months.

Manager, Enterprise Sales

TapInfluence

TapInfluence acquired by IZEA July 2018

Brought in by executive team to build direct SaaS sales engine, and aggressively drive the adoption of TapInfluence platform across enterprise brands & agencies through creation of scalable outbound sales model, and overhaul of lead to cash process. 

Instrumental in closing large enterprise $100k+ ARR deals with Comcast, Boulder Brands, Demand Media, and other large PR and Advertising agencies to jumpstart SaaS model.

Enterprise Sales

I help sales professionals elevate their communication and customer experience with video messaging. With over 15 years of experience and expertise in SaaS sales and enablement, I have a deep understanding of the challenges and opportunities that sales teams face in today's competitive and dynamic market.

My passion is to modernize the sales profession and transform the way salespeople connect with their prospects and customers. I have a proven track record of building and leading high-performing sales teams and enablement functions at fast-growing SaaS companies, such as Zoom, where I helped the company grow from $100M to $4B in revenue in 3+ years. I believe that selling is not about pushing products, but about helping customers achieve their goals and challenging the status quo. 

Let's work together to lift each other up and maximize our potential.

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.

LinkedIn Login, Sign in | LinkedIn

JSESSIONID

li_at

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

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.

"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?!?

The best growth strategy any business owner/salesperson?

Be really fckn good at what you do. 

We can talk about the 50 metrics and different tools that can help you get better at your thing...

But at the end of the day, people want to hire people that don't suck.

You hire a plumber that was recommended to you by a friend, because they're good, fast, and professional. 

Not because they have the fanciest marketing and look good on the internet.

It sounds trite, but doing one thing incredibly well is BY FAR the best strategy to never be broke again. 

Here are a few people who prove it:

Heather Monahan - best salesperson I ever met
Tony Brophy - killer cold caller
Chelsea Olsen incredible social seller
Kellen Casebeer - PHD level message-market fit genius

...and of course... my 🌶️ side piece

Ryan Reisert - top 0.01% of Outbound Sales Operators

Who's on your list?

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Rich Adams

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