The Okta Sales Playbook That Turned $1.9M Into $1.3B+ ARR
Learn the Silicon Valley Enterprise Selling System from the Man Who Helped Build It
Meet Irwin Ki — Former Okta sales leader who helped architect the inside sales machine that transformed a struggling startup into a $16B+ public company.
While competitors with better products failed, Okta dominated through superior sales execution. Now you can learn the exact playbook that made it happen.
Answer: High-Caliber Sales Execution — the key differentiator.
The $16.5 Billion Lesson Most Founders Miss
In 2012, OneLogin was winning the SSO race. They had:
First-to-market advantage
Superior product features
Faster early traction
Then came Okta — late, behind, and underestimated.
The outcome?
OneLogin: Sold quietly for an undisclosed amount
Okta: $2.75B+ ARR, successful IPO, $16.5B+ valuation
The difference wasn’t the product. It was enterprise sales execution.
🚨 The Problem Killing 90% of Tech Companies:
Most founders think great products sell themselves. They don’t.
Right now, your competitors with inferior products are winning because they know how to sell while you're still figuring it out.
The painful reality:
90% of sales teams can't properly qualify a deal
They waste months chasing "ear sugar" prospects with no buying power
They miss forecasts, burn investor trust, and fail to scale
They don't know what a Champion is, let alone how to build one
If you don't know how to sell it, someone with a worse product will beat you. Every time.
The Silicon Valley Sales System That Changed Everything
What Made Okta Unstoppable
I was there. As an early sales leader at Okta, I helped build the inside sales engine that supported the explosive growth from startup to IPO.
Here's what we did differently:
Your Competitive Advantage: Learn From Someone Who Was Actually There
Here's what makes this different: I wasn't just watching from the sidelines. I was in the leadership boardroom learning while simultaneously executing on the ground, building and training the future sales leaders of Silicon Valley.
My track record:
Built the inside sales team that supported Okta's massive enterprise field organization
Helped grow ARR from $1.9M to $70M+ in 4 years
Trained reps who became VPs and Directors at top tech companies
Created the 5-step hiring methodology used to evaluate original Okta SDRs
Recent client success: GovInvest was struggling with 5 Jr. AEs where only 1 was hitting quota. After implementing our Silicon Valley selling changes:
Restructured to optimal 2 AE & 3 SDR pod structure
Added automation that resulted in 500% pipeline increase
Achieved 10x improvement in dials and connections
Accelerated pipeline growth without expensive new hires
What You'll Master
The Complete One Deal Away Sales Arsenal:
Elite Hiring System — The 5-quality methodology to identify and hire enterprise builders (not just order-takers)
Champion Building — How to identify, develop, and leverage internal Champions who sell for you
MEDDICC Mastery — The qualification framework that separates real deals from time-wasters
Pipeline Generation — Systematic approaches to build predictable revenue streams
Advanced Deal Inspection — 20-minute process to forecast with Wall Street-level accuracy
Audible Ready Training — Make your entire team instantly adaptable to any selling situation
The Bottom Line
You don't need millions in funding to execute like Okta. You need the right coaching, framework, and strategy.
The companies that win aren't those with the best products — they're the ones with the best sales execution.
Stop letting inferior competitors beat you. Learn the Silicon Valley secrets that turned Okta into a $13B+ company.
Ready to Build Your Own Winning Sales Team?
Get direct access to the One Deal Away sales playbook that built Okta.
Learn champion-based selling, advanced deal inspection, and elite hiring strategies from someone who was actually there.
[Schedule Your Strategy Session] [Learn More About the Program]
"Nothing happens until you sell something." — Freddy Kerrest, Okta Co-Founder
How did Okta go from $1.9M to $70M+ M in 4 years?
In the beginning (2012) there were two startups attacking the cloud Identity management or in the early days “Single Sign On” (SSO) space.
OneLogin and Okta.
Both raised money from VCs.
Both had great founders who could build a great product.
Both had market tailwinds: cloud + security + adoption of SaaS
Onelogin had the head start.
They were first to market, had a better product, and had faster early customer traction!
In 2022 the ARR revenue for OneLogin is at $50-80M vs OKTA at $1.3B. One was acquired for an undisclosed amount and the other is currently trading on the NYSE at over a $13B valuation.
Answer: High Caliber Sales Execution- the key differentiator.
Step 1: They had an Enterprise Vision and Product Execution.
Everything starts with the founder’s (Todd & Freddy) vision. They both came from Salesforce.com and Todd was in charge of building the Force.com platform in the early days. They had a vision on the future problem of the emerging SaaS eco system and was able to attract early VC’s who also had a knack at building BIG enterprise SaaS companies.
The reason why they were behind OneLogin from the start was the amount of time and effort building the foundational platform to ensure security, uptime, with the vision of attracting and supporting the largest and smallest customers.
As product matured the team had a clear vision prioritizing customer’s asks with expanding beyond just the SSO (Single Sign On) early use-case to many other product lines like mobile security, external customer identity, and much much more.
Step 2: They invested in hiring and building top talent Silicon Valley Sellers leadership.
“Nothing happens until you sell something.” -Freddy (OKTA co-Founder).
With great vision, story, and Series B VC war chest. They were able to tap into their network and hire the very best up in coming talent.
Did you know they actually had 2 VP of Sales join fairly close to each other?
B2B Enterprise sales people are a very different animal…especially the ones who I consider “Builders.” They are willing to leave the big box corporate brand to build a region, team, and revenue from scratch.
They are highly experienced, trained, intelligent, and are used to long and complex b2b sales.
They are highly sought after from other startups and enterprises. The best of the best are recruited to join the top VC funded portfolio companies.
If you are lucky to be part of this insider group. You’ll learn that they are masters in building “Champions.”
A Champion (n): Someone who has power and influence who is selling for you when you are NOT in the room.
Rookie sales people would consider themselves as sellers, closers, prospectors.
Rookie’s would fall into the many mistakes a new sales team would make.
Not having a clear “Pipeline Generation (PG)” plan.
Not having a clear sales process = inaccurate sales forecasts
Losing the deal alone vs incorporating other Champion Builders into the deal
Sounding like a salesperson vs consultative selling or industry expert
Wasting time on bad or unqualified deals.
The Rookie is NOT Audible Ready for various sales scenarios.
IMPACT: Sales Team Building is a lot like building a sports team. If you have weak players or untrained players you’ll never win a championship. This will result in loss of millions of dollars through recruiting and sunk salary costs. Missed forecasts that results in weaker VC rounds and ultimately a lower probability of a Unicorn outcome. Billions!!!
“If you don’t have a champion you don’t have a deal.” - VP of Sales
If you don’t hire or train your team to become champion builders… you won’t have deals.
Step 3: They implement the Silicon Valley sales process: This culture, language & playbooks was passed down from the OG of Silicon Valley Selling.
BACK in the early pre-SaaS days of tech. Enterprise Software was SLOW, on-prem, clunky, and required huge deployments.
There was NO such thing as an easy freetrial or proof of concept to send your prospects.
Sellers didn’t even have Salesforce.com for CRM management. It was a QBR (Quarterly Business Review) done with the reps, the sales leader, and good ole fashion deal inspection.
Yet without all the fancy bells and whistles that modern SaaS organizations have today...they closed deals. BIG DEALS.
So how did they make deals happen?
Champion based selling & Silicon Valley Sales process.
Through countless missed forecasts, chasing false deals, having deals slipped you have the literal evolution of sales from the survival of the fittest and learning from the pain of losing and winning.
These “elders” of on-prem sales that survived…eventually thrived into building the successful teams that crushed their numbers and become the future leaders who built some of the largest SaaS independent public companies (NOW, OKTA, APPD, SNOW, MDB, SUMO).
The Silicon Valley Selling Process became
Over 4 generations of sale leaders there was a standardized the language.
If heard terms like:
Champion vs Coach vs Saboteur
Pipeline Generation (PG) plan
Quarterly Business Review (QBR)
MEDDICC qualification methodology
Mutual Action plan (MAP)
Forecast commit, best case, and pipeline metrics
Sounds foreign to you...it’s because this is what the great SaaS sales teams like Snowflake, Service-Now, OKTA all the great enterprise SaaS companies understand.
There is a history of winners and losers...and the above terms and sales exercises are used to help standardize and scale a high-performing sales organization.
We have the secrets and methodology taught to get into big enterprise accounts, running complex multi-million dollar deals, and forecast it accurately.
They know how to qualify quickly and break down very complex technical concepts and map it the business initiatives they are serving.
They know how to strategically use their resources (SE, product team, marketing) to play chess vs checkers when win a competitive deal..
Until now it’s was reserved for the well funded companies who could hire the top shelf of sales leadership and the $500k-millions of enablement budget to implement it.
This program is designed for the underdogs. The tech professionals who want to learn the dark arts of silicon selling.
Whether you are carrying a quota today, or starting to build your sales process, or even if you are a manager/leader who is buying software today. There is value in learning how to SELL.
Step 4: Implement effective Silicon Valley Sales Strategy.
What is our go to market (GTM) strategy? Do we hire Enterprise, mid-market, or SMB AE’s first? Should I learn to sell first or do we hire sales development reps (SDR’s)?
Ultimately, how do we build a sales team that produces predictable revenue?
After we have the initial pod strategy lined up...how do we recruit, train, and retain new sales talent?
This is what I was brought on to help execute at OKTA.
I’m not going to take all the credit. No but one thing the founders and board did was select an up and coming CRO.
They hired my mentor and VP of Sales at the time Adam Aarons from the big public BMC Software. Adam was mentored by the legendary John McMahon (Advisor for AppD, SumoLogic, Bladelogic, etc).
Both were the 3rd and 2nd generation of the Silicon Valley Leaders.
[Insert image of Adam and Me?]
This is where I come in. I was also groomed from ex-bladelogic reps and supported them in the fiery trials of BMC Software. Where they spent millions of dollars on sales enablement and weekly product training.
Adam brought me on to build the inside sales team to support his massive enterprise field team.
And we built an incredible roaster.
The pipeline went parabolic. Many of the early sales hires become field reps and some even VP and directors themselves.
Not only was I in the leadership boardroom learning but I was also executing building and training the future sales leaders of Silicon Valley.
There are soooo many mistakes around hiring the initial sales team. Reps are
Not tested deeply in the interview process for sales experience = You’ll miss out on great potential or worse hire bullshitters
Not pre-framing needs and expectations upfront to ensure rep commitment = you hire short term minded sales people.
No training or career development path = you won’t get the most out of their potential
Culture = great culture lifts up all challenges!
It’s easy to spend a lot of money hiring to fill headcount...but a lot of mistakes are made from inexperience.
[Do we insert GovInvest case study] GovInvest had promoted SDR to 5 Jr. Account Executives with resulting only with all but 1 hitting their quota. With proper Silicon Valley selling changes…they were able to learn that all but 2 AE were ready to keep selling. They restructured their sales process and sales pod to 2AE & 3 SDR pod. They took my advice on adding automation for their cold calling and emailing…which resulted in 500% inc in pipeline. 10x the dials and connections. Which helped the team accelerate pipeline growth without having to hire a bunch of sales candidates.
If you have a solid inbound & outbound SDR program. You can also create a flow of candidates who can grow into an SMB->Mid-Market-> Enterprise sales career.
You’ll learn the exact 5 hiring methodology that was passed down from veteran VP of Sales and used to evaluate and hire the original 18 reps hired on my OKTA SDR.
Top 5 qualities and how to test for:
Step 5: Get everyone Audible Ready
The term “Audible Ready” is from american football where the quarterback calls an “audible.” to get the entire team to change the pre-huddle plan to a different play in the present moment!!!
Getting your sales messaging and team audible ready is of utmost importance.
This is what the great sales teams do.
Clarity of sales messaging, the different plays to build the champion, giving new reps the enablement content and strategies to be “Audible Ready” when ready.
Being audible ready to write an b2b executive email, execute a pipeline generation (PG) plan, forecasting your deals to your manager, answering objections with your customer, when you cold-call an executive...your team's Audible Ready capabilities is key for them to be empowered to go and run grow their business.
With a culture of Audible Ready first. You’ll get everyone ramped faster and on to closing business sooner.
Step 6: Execute & Iterate Silicon Valley Advance Deal Inspection.
Learning how to manage a sales team and forecast accurately is #1 challenge leaders have a difficult time at every organization.
Why? It’s hard to distinguish the BS from great sales people. You’ll want to hear their pipeline really is in the millions of dollars...and the deal you are depending on is x
There is a very simple process to get your
Have you wonder how in the world do sales teams and leadership forecast accurately? Especially when they are a public entity reporting to Wall Street?
They know how to do “Advanced Deal Inspection.”
The understand how to train and manage what they are looking for during their Sales forecast meetings.
Advance Deal Inspection is a very tough process to look through each pipeline, best case, commit deals to find the gaps in the deal to help separate the “FLUFF or Ear Sugar” that the prospect has told your rep to defining the necessary Mutual Action Plan (MAP) that both the seller and buyer needs to create in order to close a complex deal.
The sales process & language of categorize deals for forecast is an art & science that is executed in the Silicon Valley Selling Sales process.
Silicon Valley Sellers are able to evaluate a deal in less than 20 minutes.
They have to make strategic decisions while fighting the end of week/month/quarter.
By understanding how to inspect a deal new actions and strategies can be executed.
This is why great sellers close deals 5x faster and with close to 100% accuracy.
Other notes I didn’t add/keep:
They are experts in their field, consultants to customers and are able to qualify quickly, iterate in whitespace territories and ultimately sell effectively!
Unique Insight Intro: only the top VC funded startups have access to hiring these sales leaders.
The best reps and teams float to the best products…they cost a shit ton 350-500k + equity. And are constantly pursued by competitors and big tech!
Coming from Salesforce.com...the founders know that they HAD to build a killer sales team and equally important they had to invest a lot of time building the platform to be enterprise ready.
Ready for security hoops and to handle the load of having millions of requests without over going down.
The first selling year was the hardest.
They had to sell a solution that only had a few SaaS intervention. Salesforce and Gsuite:
They Hired a couple AES had small 2 SDR who were struggling to produce real pipeline.
The team was good. Getting initial traction to over a $1M in sales.
It was a concise decision to raise the money needed hire a true enterprise SaaS team.
BUT needed leadership to scale & EXECUTION.
Here is a Quick history lesson of Silicon Valley Selling.
Intro: Irwin your Silicon Valley Advisor
Unique Insight: The sales people know how to build sales champions. What are champions?
“Champions are people with power & influence who are doing the SELLING for YOU when you are not in the room.”
In the greatest of Enterprise Sales teams. You can tie many CRO’s to the godfather of SaaS CRO.
I’ve been in the fortunate position to sell as an operator and get first hand knowledge & execute the Silicon Valley Selling methodology in building OKTA’s first inside sales team.
After bringing me in. The whole inside sales process had to be redone. Started from 0 SDR...hired & trained 5 new AEs from scratch and by the second quarter the team produced 108 opportunities resulting in $500k in new pipeline for the team.
The process was repeated and grown quarter after quarter...
The legacy of how to sell has been passed down from the OG of Silicon Valley Sellers to their AE who become managers and are on the hunt to create their mark as a CRO.
These insights
They practiced “Champion Based Selling”
A4
“Here’s the truth:
You can achieve build or enable a great sales team using Irwin.
However, there is a {problem} because of {reason}.
We are the best/only people dedicated to solving this problem for {niche}.”
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