Can AI/ML continue to make waves in HR Tech? A dive into

Another day, another diligence memo! Today I focused on a company in the HR/Talent Acquisition space.  For this one, it wasn’t done around a specific deal, simply about the company overall.

Company: Headstart



Key Takeaway

  • An AI/ML focused startup that has the potential to disrupt the HR/Talent Acquisition landscape through focused execution and a diligent leadership team.  Initial traction between users and corporate accounts demonstrates execution and upside potential but tempered by intense competition and fears of this being a feature and not a full-fledged company.


Company Description

  • Headstart is a developer of a job matching platform designed to help employers identify the best-suited candidates in the shortest amount of time. The company’s platform utilizes machine learning technology and combines psychometric testing and algorithmic analysis to offer effective, engaging and unbiased applicant review, enabling job-seekers to connect directly with businesses and companies and save time and money by accurately finding candidates who meet their exact job recruitment. The Company’s ability to combine traditional objective job traits with context and cultural fit of the target company is their key differentiator. They recently participated in Y Combinator’s Summer 2017 batch. (source: PItchbook, company website)

What could make Headstart a success? What could make it struggle to succeed?

  • Headstart could be a success if it can continue to provide positive outcomes for its large corporate clients while not losing sight of the job seeker experience.  This balance between serving two-sided marketplaces is fraught with peril so appropriate consideration must be given to not only the job seeking user experience but also the corporate user and their KPIs around time to hire and using the algorithms to find strong cultural fit.
  • Headstart could struggle to succeed if the Company’s algorithms do not improve candidate selection metrics for its corporate customers. It could also struggle to succeed in acquiring job-seekers amidst hundreds of other competitors and have low conversion rates for the target companies and high customer acquisition costs.

Market Potential

Talent Acquisition Segments 2016   ($M) 2021 ($M) CAGR, %
Applicant Tracking 732 889 4.0%
Contingent Labor Management 445 578 5.4%
Marketing 410 514 4.6%
Onboarding 447 545 4.0%
Recruiting 1,219 1,450 3.5%
Sourcing 728 782 1.4%
Total 3,981 4,757 3.6%
  • Source: Apps Run The World, January 2018

The talent acquisition market within HR tech is expected to reach $4.7BN by 2021.  This is a massive opportunity for Headstart to continue to break into this market. That said, the majority of the market is currently made up of by the big names in the space (LinkedIn, IBM, SAP, etc.) but there is continued interest in new/emerging technologies which could drive greater adoption for Headstart.
talent acq

Management Team

    • The team is led by two co-founders with backgrounds in edtech and a Thiel fellow as well as neuroscience/ML/AI. The two co-founders combined with their extended management team have all the makings of a strong team poised to execute well and their ability to attract large corporates as well as YC backing, especially the AI Vertical group, is a testament to this ability.


  • Nicholas Shekerdemian – Co-founder (CEO)


      • NIcholas is a Forbes 30 under 30, a Thiel Fellow, and also started an online tutoring/consulting edTech company focused on China and the UK prior to founding Headstart.  Just age 23, he seems dedicated, driven, and passionate about enacting real change in the talent acquisition market


  • Jeremy Hindle – Co-founder (CTO)


    • Jeremy is a Forbes 30 under 30 with a strong background in neuroscience, AI/ML and programming


  • Headstart was recently accepted into Plug and Play’s enterprise 2.0 batch for 2018.  Prior to that, the Company was in YC’s summer 2017 batch and before that the company bootstrapped itself. According to Pitchbook, total financing is at $120k but a few other sources have the total raised at $600k.  
  • Regardless of true total raised, the Company has shown strong capital efficiency in that it grew its team from bootstrapped 2 co-founders to 17 employees all on a minimal amount of investor capital which combined with their customer adoption, leads me to believe they are generating decent initial revenues.  
  • Headstart’s ability to drive solid adoption and close corporate customers while bootstrapping and on minimal capital is a very positive development and demonstrates their ability to effectively manage capital yet still execute on the business.


  • The competition in Talent Acquisition and the broader HR tech landscape is immense.  Competitors range from multibillion dollar companies to well-funded growth stage startups to a handful of other early stage businesses.  This provides market validation of the need for new approaches to recruiting but also makes the potential for success that much more difficult.  
  • LinkedIn, Glassdoor, ZIpRecruiter, Lever, Indeed, Smartly, and many others are just a few of the companies vying for a similar budget that Headstart is going after.
  • A lot of the competition is looking to differentiate in certain ways via metric tracking (Lever), mass market adoption/1st mover advantage (Linkedin), education/value add services (Smartly) and Headstart is no different. Their focus on AI/ML to drive comprehensive hiring is a strong differentiator if they can execute on it.
  • Koru appears to be the closest direct competitor I could find to Headstart in that it is also aiming to get predictive on hiring based on more than objective criteria for those early in their careers.  According to Pitchbook, they have raised $15m to date but it looks like they did a Series A2 in Sep 2017 at a down round from their Series A in 2015. They did have a solid investor syndicate in their Series A (Battery, First Round) so I would want to dig further on Koru and look to connect with their investors or the company itself to get a better sense of what caused the down round and if it was company execution or more macro issues and use that for guidance with Headstart.

Financials/Growth/KPIs/Business Model

  • The Company has had solid success in its first year of founding, they have over 100 corporations signed up and over 20k students signed up.  The business model is corporations pay for posting and using the service whereas job seekers and small start-ups can use the platform for free.  
  • Similar to the Company’s capital efficiency, their ability to attract sizeable numbers of students and corporations all while growing the team substantially is a positive indicator about future upside.  I would want to learn more about the Company’s customer acquisition channels and how they plan to fulfill both sides of the market while maintaining growth and managing cash burn.
  • One of the biggest questions i have regarding Headstart as a potential investment opportunity is their focus on expansion.  Do they plan to really build out a true double sided market and become the next LinkedIn/ZipRecruiter? Or are they comfortable using their algorithms and matching software as more of a traditional enterprise sale or feature to then be built into a larger platform such as LinkedIn’s offering.  I find it would become fairly cost prohibitive to go after the double sided market given the large incumbents but I could see more viability in focusing on the corporate clients it just may become more difficult to effectively train their algorithms with less job seeker data.
  • For KPIs, I would want to learn about their CAC, their Sales cycle for corporations, their average sales price, their revenue concentration by client, their churn, their conversion rates from candidate to being hired, and their ability to truly tailor candidates to more than just a job description and really source for culture.

Key Strengths

  • The team’s ability to execute on minimal capital and drive substantial initial results is by far the most impressive thing to me so far.
  • The AI/ML angle is the second most impressive potential strength. If the company can continue to prove their offering and their algorithm can match better candidates for fit/culture then they will truly be an outsized venture-level success in market.
  • The HR tech market is also a strength as there is a lot of appetite for new products and an ability to prove ROI on recruiting via time or cost savings.
  • The user experience on the consumer user side can also be seen as a strength as they appear to be able to have a single application/profile for each user which drives ease of use and easier adoption.

Key Risks

  • Can the company achieve scale? They have gotten initial validation and some key customers but can they really achieve growth on both sides of the market to feed their algorithms and continue to amass the dataset needed to truly change the market around talent acquisition?
  • It appears they have lost their head of Psychology/Psychometrics based on his updated LinkedIn profile.  Can the company continue to achieve scale with the right management team while dealing with turnover/hiring their own candidates?
  • With any AI/ML or algorithm approach, there is always risk that someone else can make a similar algorithm and/or a “better mouse trap”. How do you view your IP/Algorithms as defensible to the major incumbents (LinkedIn, Google, etc) and what is stopping them from using their vast user base and data sets from creating a similar offering?

Key Questions for Management

  • What information is needed to best feed the algorithm? Job seeker data or corporation data?
  • Is acquiring Job seekers vital to the algorithm and if so, how do you plan to profitably acquire users at scale? How has using school groups and ambassadors worked so far?
  • Koru the company – are you aware of them and their history? If so, did they have any issues in market or just company specific issues?
  • What are your expansion plans? WIll you look to raise traditional venture growth funding or plan to run the business via sales/profitability using corporate customers?
  • What has been the feedback from current customers? Has there been any churn? If so, what was the reason for the churn?

Final Thoughts

  • I think Headstart has a lot of upside and has shown their ability to execute on minimal outside capital. I think they have a strong team and are hitting the timing right with their focus on AI/ML in market and the appetite for corporations to utilize new technologies to recruit the best candidates. This combined with their recent acceptance into Plug and Play’s 2018 Enterprise 2.0 batch makes Headstart a company I will continue to follow and recommend for further diligence.

Series A Teardown – Front

This is my first run at a teardown of a Series A Company.

I am going to try to make this a recurring theme where I dive into a publicly available Company pitch deck and derive an investment and due diligence memo from it.

Why? Because as a VC-nerd I find this fun but I aware I probably need more hobbies 🙂 In reality, I hope this can provide a framework into how I look at certain types of companies in various sectors.

Company: Front



Front Original Slide Deck  – Series A, 2016

Key Takeaway

  • A promising company with solid initial traction and potential to warrant a continued look.

Company Description

  • Front is a collaboration tool for enterprises. It is a multi-channel email system that provides a unified view and allows teams to collaborate across the enterprise.  

What could make Front a success? What could make it struggle to succeed?

  • Front has good initial traction and has been very capital efficient since inception. This financial rigor combined with an ability to scale and generate consistent growth could allow them to achieve a sizeable outcome.  
  • Front could struggle if they cannot transition from organic growth to paid growth to effectively reach scale and if other major players in the communication space decide to build a competing product.

Market Potential

  • If executed properly, Front has the potential to take share from the external communications, support, and customer service industries, a billion dollar business is feasible.

Management Team

  • The Head of Sales is the former 1st salesperson at Box and the Head of Customer success was head of upsells at Dropbox. This seems to be a quality team for entering the market.


  • Front participated in Y combinator and then raised a $3M Seed round in 2014 from notable angels including Elad Gil, Dave Morin, Alexis Ohanian, and Paul Buchheit.


  • Combination of established players and growth stage/VC backed companies

competition front


  • Front has signed up a few major brands and other lighthouse customers but the extent of their revenue concentration from these customers is unknown.  I would want to understand more about how much MRR these select customers were responsible for before passing judgement on whether these are true customers or just marketing ploys.

Financials/Growth/KPIs/Business Model



  • For the sake of this exercise, I am assuming that pricing hasn’t changed since 2016 from what is on the current website.
  • This is clearly a high volume, low price per user business.  The company employs a land and expand strategy where they sign up individuals and small teams and then look to upsell and cross-sell to the rest of the organization.  
  • Bonus points for the 14 day free trial as well as the annual pricing with the 17% savings highlighted as each plan is billed annually upon sign up resulting in cash inflow from day 1 as opposed to monthly. This sales incentive to generate cash flow is part of the Company’s financial rigor that I am impressed with.

MRR and Customer Count

  • The company has shown consistent and impressive MRR growth and increased customer adoption.  This is excellent to see this consistent early traction with no marketing spend
  • That said, doing an estimated MRR per customer shows a different story. As seen below, the average MRR per customer shows a continued decline.  While it is great they are growing both MRR and customers, it appears that the average MRR per customer is decreasing each month meaning that less and less seats are signing up per new customer.  
Estimated MRR, Customer Count
Date MRR Company Count Avg. MRR per Customer
9/1/14 $15,000 62 $242
12/1/14 $26,000 125 $208
3/1/15 $41,000 200 $205
6/1/15 $59,000 330 $179
9/1/15 $82,000 500 $164
12/1/15 $97,500 670 $146
3/1/16 $113,000 880 $128
*my estimated calculations by reading the graph in more detail
  • I would continue to monitor this trend as it could be a sign of trouble should the average keep getting lower and lower.  I understand that this is a freemium/self-service type SaaS model with low barriers to adoption but this is something that worries me especially for when they have to move to paid advertising to attract customers and the resulting LTV/CAC ratio could be based on drastically lower LTV expectations.

User Churn


  • Front advertises low churn and negative net MRR churn. While the negative dollar churn appears to be true, the 3% monthly user churn seems a bit high to me as that annualizes out to about 31% user churn which at 1000 customers would be 310 lost customers a year! I understand that this is a high volume business but that is a dangerous amount of customers to lose even at this early stage.  
  • I would want to learn more from management as to the main causes of churn

Dollar Churn

dollar churn.png

  • On the flip side, I am impressed with their successful expansion strategy and the resulting negative net MRR dollar churn.  The ability for the company to replace not only the dollars lost from the churned users through greatly expanding MRR from retained customers has been very impressive.  Especially impressive has been the ability to continually increase the MRR on an annual cohort basis of 150% of starting MRR. This helps prove their product is not only viable for its initial customers but that Front can successfully upsell consistently over time.
  • Conversely, if my calculations on average MRR per customer are correct, the absolute dollar value of MRR expansion may not be as impressive on the more recent cohorts. Seeing that Average MRR per customer has decreased from ~$240 to ~$130 since the cohort measurements started, getting to 150% annual expansion of $130 MRR would only generate $195 in MRR so the expansion of a lower starting MRR customer is less impressive on a percentage basis. While it is nice to see that they can land and expand, if the starting point continues to get smaller it may be a cause for concern.
  • I would want to ask management more about their customer dynamics around free trial conversions, customer revenue concentration within each cohort, and expansion strategy playbook.

Capital Efficiency

cap effic

  • To me, this is where Front shines.  The fact that they have only spent $1.3M to arrive at $1.4M in ARR is extremely impressive especially given how much companies are spending on customer acquisition, engineering talent, and perks these days.  
  • The other impressive piece is they still have over half of their Seed round left. That and their $90k monthly burn rate gives them about 20 months of runway so even without this $10M they are still on solid financial footing.



  • Front expects to triple ARR in 2017 and while this would be impressive, it is unclear where that sales efficiency would come from based on this financial plan.  I would want to ask management a lot more questions around how they plan to build up this ARR and what the “Other” expense entailed as it is unclear if this is salary for sales, rent for a building, etc.
  • The non-engineering spend seems to taper off starting in February 2017 so it appears they expect to hire aggressively through the end of 2016 but less so in 2017. I would be curious to know their hiring plans as well as their sales and marketing plans.  


  • According to Pitchbook, the Company raised their $10M at $30M pre for a post-money valuation of $40M.   While I am unsure the validity of these terms, this could be an appropriate valuation for the round given the Company traction.  While you can’t really use public company multiples as a comparison given the differences in company profile, a few other methods could give us comfort.

VC Ownership Method

  • From a venture ownership, this follows the more traditional model of investors owning ~25% of a company in the series A so that isn’t out of the ordinary and what i believe had an outsized influence on this valuation and pricing of the round.

VC Rate of Return Method:

  • If Front raised $10M, Series A investors would expect a $100M return (10x) which would be $400M in exit value which in the realm of B2B SaaS deals is more than reasonable.  With major corporations spending hundreds of millions and even billions in M&A each year combined with the ability for companies to IPO at the $100M revenue threshold on a path to profitability, the options for an exit of this caliber are fathomable if Front can execute on their vision long term.


  • Front’s value proposition, its capital efficient growth, and capable management team have demonstrated enough value to warrant a sizeable uptick in valuation from their seed round.  I recommend we continue further diligence with management.

Disclosure: My employer (SVB) may do business or seek to do business with companies mentioned or their competitors. Views expressed above are solely the views of me.