Siro’s Top Secret Master Plan

Field Sales Careers Change Lives

No careers offer better earnings potential and a lower barrier to entry than careers in Field Sales.

Most blue-chip college graduates will be surprised to learn that there are field sales professionals without college degrees out-earning doctors, corporate lawyers, and software engineers. Jake made more money per-month selling Cutco knives at 18 than he did later as a business analyst at McKinsey.

But the impact is more than financial. The skills learned in Sales are some of the most transferable, human, and AI-proof skills you can learn.

If Joe had never tried sales, he would never have acquired the risk tolerance to found a company.

If Jake had never tried sales, he would never have built the resilience to secure VC investment.

Our favorite thing about sales is the opportunity it offers to those who try it.

Our least favorite thing is that, overwhelmingly, most new reps never receive the coaching they need to take full advantage of it.

But most Sales Reps Fail

For some, sales roles are a gateway to financial freedom, but for most, sales roles are a constant struggle.

Individual sales productivity follows a Pareto distribution, meaning that the vast majority of commissions accumulate to a small group of excellent sales people.

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The majority of sales reps will never come close to the income levels or financial freedom realized by the top producers.

Lopsided productivity curves like this are ubiquitous in sales even in top performing organizations. When I was the sales manager for Vector Marketing’s Paramus office, we finished in the top 2% of teams in the company, and our reps’ sales productivity still followed a Pareto distribution.

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This begs the question: How can we help struggling reps become more productive?

Productivity Tools Aren’t Enough

Companies building sales productivity tools, like SalesForce, have made a lot of money because they add productivity gains to sales teams. Tools to “scale sales reps” with automation, gamification, training platforms, and workflow tools significantly increase sales output across a sales team, shifting the sales distribution curve to the right:

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However, the vast majority of sales reps still fall below the “financial freedom” threshold.

To meaningfully increase the number of sales reps that find financial freedom through sales, we need to change the shape of the curve.

So what makes the curve so lopsided in the first place?

The Problem is Coaching Scarcity

August 2017 in the Jordan household:

Joe: “Alright mom I’m heading to the sales meeting

”Joe’s mom: “I thought you were quitting?”

Joe: “So did I”

When Joe decided to quit sales (or so he thought), his manager pulled her car over, and they had a 45 minute heart to heart on the phone. She talked Joe out of quitting, and Joe will forever be grateful that she was there when Joe needed it, but interactions like this one, where a manager truly invests in and impacts a single sales rep are the exception, not the rule. As sales managers, Jake and Joe were so time constrained that they had to begin selectively coaching the most promising reps in a new cohort of sales reps as early as their first day.

Sales productivity is so skewed because good coaching is scarce.

The number one reason salespeople quit is lack of coaching, and the number one lever for sales productivity is coaching. Yet, 48% of sales reps aren’t coached at all, and most who are only receive coaching once a month.

But sales management is not at fault. Coaching is hard.

Coaching someone well requires listening to their sales conversations or role playing, reviewing their sales and pipeline data, and finding time to discuss goals and address skill gaps.

This requires time and attention. It’s a skill that needs to be trained and is often very different from the skillset that got a coach into their current position. And finally, coaching is not uniform. Different people require different coaching styles. A great coach can adapt to the style of the student (rep), but even still, no coach has the range to help every learning style.

As a result, only the most promising reps get meaningful attention from their manager, and only the luckiest of them have a manager that is also an excellent coach who they can relate to. The promising and lucky end up at the financial freedom tail, and the rest are left behind.

To change the shape of the distribution, we need to make coaching abundant.

Disclaimer: Of course, some people are less responsive to coaching and will not improve even with aggressive coaching intervention. Someday we may find a way to help this group, but this group represents a minority of sales reps.

Scalable Coaching Is Now Possible

To make coaching abundant, we need to remove the dependency on a single coach who has limited bandwidth and whose coaching style can’t serve everyone.

Technically, we need software to extract and deliver insights from sales conversations at scale. Thanks to recent advancements in AI and audio processing, this is now possible.

While building Alexa in 2011, Amazon had to acquire an entire company, Yap, for it’s speech-to-text technology. At the time of the acquisition, Igor Jablokov, the CEO and co-founder of Yap, called speech recognition “one of the most arduous tasks in computer science.” Fast forward to 2021, and Azure, AWS, IBM, GCP, and several new startups all have their own speech-to-text APIs, making speech recognition exponentially more affordable and available.

Just as smartphones fueled the social media boom and cloud computing fueled the SaaS boom, speech recognition APIs and other advances in machine learning will fuel the boom of conversation intelligence, a new industry comprised of applications that analyze recorded conversations.

Siro was built to take advantage of these advancements and wield them to scale sales coaching and break the lopsided distribution of sales success, which data suggests is possible — A study by Harvard Business Review found that a data-driven sales coaching approach helps the bottom quartile of sales reps improve by 200%, while helping top sales reps improve by 50%.

For the first time, we have a chance not just to shift the productivity curve, or to bend it slightly, but to fundamentally change its shape, helping more reps achieve financial freedom than ever before.

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Top Secret Siro Master Plan (just between you and me)

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Step 1: Scaling the Sales Manager [LIVE]

Siro’s first step is to scale the sales manager by recording their reps’ sales conversations, analyzing them, and surfacing the most coachable moments from them to their Siro inbox - making coaching as easy as responding to a text message.

Our beachhead market is consumer field sales teams, where Jake and I got started in sales and where managers normally would have to drive or fly to observe their team’s sales conversations without Siro. With Siro, coaches have been able to review conversations 10x faster, enabling them to coach their entire team once every few days instead of once every month.

Scaling the sales manager allowed us to impact over 3,000 sales reps with a bootstrapped product.

Step 2: Reps Coaching Themselves [LIVE]

Scaling sales managers helps, but it still requires managers to carve out time for coaching, and it doesn’t help sales reps who have a different sales style from their manager.

Siro’s second step is to empower sales reps to coach themselves with an “answer key.” For each moment in a conversation where a sales rep struggled, Siro shows the sales rep how top reps successfully handled similar situations.

Reps need coaching that is relevant to their current challenges. Classroom style training lectures, online training content libraries, and existing conversation intelligence apps bombard reps with abstract sales concepts and random best practices that are neither retained nor implemented.

Our “answer-key” method keeps coaching relevant by starting with each rep’s real customer interactions and matching those experiences with inspiring and educational peer examples - all without relying on their sales manager’s time or ability.

Step 3: Siro Coaching Reps [Early Testing]

Allowing reps to coach themselves is valuable, but it still requires that a company has great sales reps of all sales styles, that sales reps take the initiative to listen to their examples, and that they have the ability to transform examples into learnings.

Siro’s third step is to provide direct coaching in the absence of examples from top reps. That is, for Siro to intelligently distill the most important coaching nuggets for a sales rep, and deliver this coaching so that it is easy for the sales rep to understand and take action on.

This is step 3 because it requires the most data and the most advanced AI, but recent advancements in audio processing and speech to text make this very possible.

Direct coaching from Siro enables any salesperson to receive truly world-class coaching that is not limited by the time and abilities of either their manager or their peers.

Where Are We Now?

(as of summer 2023)

Before founding Siro, we (Jake and Joe) built and scaled our first sales software company, Queue, to $100,000 annual recurring revenue and over 100,000 users in ~1 year part-time by selling subscriptions to sales teams at our former company, Vector Marketing.

In late 2020, Jake left his job at McKinsey, and we founded Siro. With a belief in the potential for software to serve Field Sales, we were accepted into the Alchemist Accelerator’s Class 26 and spent 6 months speaking with salespeople to test ideas.

In 2021, we built phase 1 of the product, acquired paying customers, onboarded over 3,000 sales reps to the platform, raised a pre-seed round, and been accepted to Grand Central Tech’s latest cohort.

In 2022, we built phase 2 of the product, hired our first employee, became cashflow positive, and built a repeatable sales process.

In 2023 (so far), we’ve begun building phase 3 of the product, grew our team to 8, became profitable, and raised a seed round in one of the hardest VC markets of recent memory.

You can see a demo of Siro here, or listen to Joe discuss our progress on the Solarpreneurs podcast here or the D2D Podcast here.

Up next for Siro is to execute on phase 3 of our journey, creating an intelligent AI that can extract coachable insights from a sea of data, and inventing a novel interface for humans to be augmented by AI.

If you’re scrappy, excellent at what you do, and excited about building a great company from the ground up, consider joining our team.

The World After Siro Succeeds

Conversation intelligence is already a $5B market, and it’s projected to grow by $27B in the next 8 years to $32B. By then, conversation intelligence will be nearly as big as the current CRM market, in which the top 10 players average over $2B in revenue and $20B in valuation.

The market opportunity is exciting, but we get up every day and work hard because of what success for Siro means.

Americans today are struggling to do better than their parents. Barriers to entry into most high-income careers have increased (e.g. college tuition), and wages have decreased or stagnated.

Meanwhile, some sales organizations will hire anyone with a social security number and those who become top sales reps will out-earn many workers who have studied for years to secure jobs in tech, finance, medicine, and law.

With a uniquely low barrier to entry and a high income ceiling, sales should be a vehicle for financial freedom, but, at least for now, it’s still broken.

Success for Siro means riding the wave of LLM and audio processing advancements to unicorn status and helping millions of people across the globe receive the support to achieve financial freedom through Sales.