How to Know if You’re Making the Right Career Move

Recently, I watched one of the most talented sales leaders I know “leave network” (quite courageously) to work at Udacity, a workforce transformation platform that helps individuals, corporations, and governments up-skill their workers in data science, AI, autonomous systems and software development. With AI likely to disrupt 47% of all jobs by the mid-2030s (according to an Oxford study by Carl Benedikt Frey and Michael Osborne), Udacity is prime to meet a significant market need when it comes to closing the global skills gap. 

For background, there are ecosystems within tech. Founders, board members, and investors build companies. Those companies sell for a lot of money. Then, those same people go out and build new companies and pull over all the same talent that got them to the last big exit. This hiring strategy is called “staying in-network.” Despite the risks this approach poses to diversity hiring, it’s not a bad strategy, and great careers have been built this way. If you’ve found a dream team, why not stay with the dream team? 

When Alex Varel, Udacity’s VP of Enterprise Sales, asked Will Reed to help build his team at Udacity, we knew candidates would likely perceive this role as a big career pivot. Candidates that would be qualified to sell Udacity would likely have spent their careers selling high-tech tools to IT leaders (versus a learning platform) and would come from a set network of companies. Leaving that network would be hard.

Despite this challenge, we’ve seen top candidates from well-funded, technical startups choose Udacity. Why?

Top sales leaders have a formula to evaluate a job change that removes emotion and gut-reactions: Company Evaluation + Market Evaluation + Personal Evaluation = Informed Decision. Using this formula, Udacity often came out on top for them, ahead of amazing alternative opportunities.

Company Evaluation

For the Company Evaluation, it’s important to look at three things: the core product, company financials, and the leadership team. It was clear from Udacity’s hockey stick growth that the platform was meeting a real need through its B2C offering, which empowers individuals to advance their careers through tech education built by industry. For an enterprise B2B seller though, that may not be enough. To succeed in the B2B space, a company needs both a product-market fit and sales fit. Candidates often asked, “Would Udacity meet a big enough need to unseat a company’s other budgeted projects?” My answer was always, “Yes!” Udacity's six-figure average deal size, productivity metrics, and 90-day sales cycles are all strong indicators of its product-market-sales fit. In partnership with good investors and strong sales / product leaders, Udacity’s sales fit checked all the important boxes for the Company Evaluation portion of the formula.

Market Evaluation

When it comes to market evaluation, it’s important to focus on the two T’s: Total Applicable Market (TAM) and Timing. Does this product reach enough customers? Is the market ready? Nationally in 2018, corporations spent around $87.6B on corporate corporate training and development and it’s continuing to grow year over year (Training Magazine). That’s a strong TAM for Udacity. In regards to timing, the market could not be more poised for a solution. Almost daily it seems, the headlines reflect this. Amazon plans to invest $700M by 2025 to train 100,000 workers for higher-skilled jobs. PwC recently announced a $3B global training initiative for its workforce to take place over the next 3- 4 years, just to name a few. Heck, Andrew Yang has built his entire presidential campaign on this seismic workforce change.

Personal Evaluation 

Finally, candidates must make their own Personal Evaluation. We recommend that candidates list out all factors that might influence their career decision (comp, title, location, travel, culture, leadership, role scope etc.) and put them in ranked order. Then, candidates should weigh their options against these key priorities. For one candidate who chose Udacity over a leading data-warehousing startup valued at nearly $4B, it came down to wanting this moment in his career to be about building a sales program versus executing within an existing program.  

“Leaving network” can seem scary, but with objective evaluation, what initially appeared to be the riskier option may in fact clearly win out.