How Okta Went from $1.9M to $70M+ ARR in 4 Years
And How You Can Steal the Silicon Valley Sales System Behind It
In 2012, the Single Sign-On (SSO) race had a clear front-runner: OneLogin.
They were first to market, had the better product, and faster early traction.
Then came Okta—late, behind, and underestimated.Fast forward:OneLogin sells quietly for an undisclosed sum (estimated $50–80M ARR)Okta hits $1.3B+ in ARR, IPOs, and trades at a $13B+ valuation
The product was critical—but many great products fail. What made Okta a rocketship was the enterprise GTM execution that brought that product to market with precision.
They were first to market, had the better product, and faster early traction.
Then came Okta—late, behind, and underestimated.Fast forward:OneLogin sells quietly for an undisclosed sum (estimated $50–80M ARR)Okta hits $1.3B+ in ARR, IPOs, and trades at a $13B+ valuation
The product was critical—but many great products fail. What made Okta a rocketship was the enterprise GTM execution that brought that product to market with precision.
Answer: High-Caliber Sales Execution — the key differentiator.
🚨 Here’s the Problem:
Most founders and tech teams think great products sell themselves.
They don’t.
In fact, if you don’t know how to sell it—someone else with a worse product will win.Even now, 90% of startups and sales teams:Don’t know what a Champion is, let alone how to build oneCan’t qualify a deal properly
Waste time on bad leads or “ear sugar” prospectsMiss forecasts, burn investor trust, and fail to scale
They don’t.
In fact, if you don’t know how to sell it—someone else with a worse product will win.Even now, 90% of startups and sales teams:Don’t know what a Champion is, let alone how to build oneCan’t qualify a deal properly
Waste time on bad leads or “ear sugar” prospectsMiss forecasts, burn investor trust, and fail to scale
🧠 Here’s What Okta Did Differently
✅ Step 1: They Built for the Enterprise
“Nothing happens until you sell something.” - Freddy (OKTA co-Founder).
The founders (Todd & Freddy) weren’t guessing. They came from Salesforce, built Force.com, and knew the pain points of emerging SaaS.Instead of rushing to market, they took the time to build a scalable, secure platform—and then wrapped it in a vision that spoke to big customers.
The founders (Todd & Freddy) weren’t guessing. They came from Salesforce, built Force.com, and knew the pain points of emerging SaaS.Instead of rushing to market, they took the time to build a scalable, secure platform—and then wrapped it in a vision that spoke to big customers.
🔥 Step 2: They Hired Elite Silicon Valley Sellers
Most sales hires are transactional. Okta recruited enterprise "builders"—reps who knew how to start from zero, hunt whales, and turn cold leads into multi-million dollar deals.They built a culture that knew how to:BACK in the early pre-SaaS days of tech. Enterprise Software was SLOW, on-prem, clunky, and required huge deployments.
- Identify Champions (influencers with internal political power)
- Qualify like pros using MEDDICC
- Generate pipeline systematically
- Run real deal inspection and forecasting (not hope-based selling)
This wasn't theory. It was execution.
Step 3: They Installed the Silicon Valley Sales Playbook
Want to know what every top-performing SaaS company (like Snowflake, AppDynamics, ServiceNow, MongoDB) has in common?They speak the same language:Champion vs Coach vs SaboteurPipeline Generation Plans (PG Plans)Mutual Action Plans (MAPs)QBRs and Deal ReviewsMEDDICC qualificationAudible Ready messagingThis wasn’t taught at school—or even most sales bootcamps.
This was handed down by legends: John McMahon, Adam Aarons, and the “OG”s of SaaS selling.
This was handed down by legends: John McMahon, Adam Aarons, and the “OG”s of SaaS selling.
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
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.
[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:
- Integrity
- Coachability
- Intelligence (EQ & IQ)
- Hunger (Fire in the Belly)
- Humility & Sales Presence
Step 4: 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.
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 5: 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.
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.
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.
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.
Takeaway:
If you're building a sales team today — especially in tech — you don’t need millions in funding to execute these methods. With the right coaching, framework, and strategy… you can scale just like Okta did.
Learn the secrets of Silicon Valley Selling — with Irwin as your advisor.
Learn the secrets of Silicon Valley Selling — with Irwin as your advisor.
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