Two years ago, we started Upsider to make the hiring process more predictable and data-driven. We spent nearly 15 years hiring and building our own teams, and our initial blog post discussed how frustrated we were with the hiring process – ponderous, labor-intensive, unpredictable, expensive. It was the hardest part of our jobs, to be honest. We weren’t sure how to fix it, but given our own less-than-pleasant experiences, we knew it needed to be done.

Our founding team has extensive backgrounds with the data-driven solutions available to marketers and investors. So we thought, why not apply a similar data-driven model to the world of recruiting?

In our initial attempt to solve this problem, Upsider started by manually recruiting for a handful of companies, using a data-driven approach to introduce roles and candidates. This process was very successful, so we built technology to automate the process, which came in the form of a sales-specific hiring marketplace. This business performed well (getting to breakeven one month post-launch), but in our hearts we felt like we weren’t addressing the problem at a deep enough level, so we took another look at the issues.

Going Deeper with Data & Artificial Intelligence

After talking with nearly 100 recruiting teams about their day-to-day process and pain points, we heard a few reoccurring themes as root causes of recruiting inefficiencies:

  • Headcount plans typically come top-down, with little to no consideration for available internal recruiting resources and marketplace considerations.
  • Recruiters spend 60-85% of their time just trying to identify candidates that meet top-down requirements, which is a very manual and repetitive task.
  • Recalibration of hiring requirements based on market availability is slow and drives a lot of wasted recruiting efforts. 
  • If hiring timelines start slipping, it can lead to expensive options like 3rd party recruiters.

 To address these problems at a more impactful level, we knew we could deliver a set of data-driven productivity tools to provide better visibility into talent pools, and automate a lot of the repetitive work that recruiters have to do every day. So we doubled down our candidate-employer matching algorithm, adding more sophisticated Artificial Intelligence (AI) functionality, and applied it to a data set of millions of candidates. We built an easy-to-use interface to allow clients to quickly execute their recruiting efforts. This combination of data, AI, and software enables recruiters to:

  • Accurately forecast time and resources required to hit hiring goals.
  • Automatically identify target candidates in any city in the US.
  • Automate the outreach to those candidates to improve conversion rates.

The Results

The new Upsider platform automates 90% of the work from job requisition to screening calls. The platform specifically addresses the biggest pain points we heard from recruiters, and initial results have exceeded our lofty expectations. A few examples:

  • A cloud infrastructure provider leveraged the Upsider platform to have an immediate impact on their hiring speed. Upsider candidate-identification AI allowed them to increase their sourcing velocity by 4x, freeing up their recruiting team to spend more time on strategic and customized outreach. They were able to use fewer recruiters on the roles while filling the hiring funnel 5x faster, increasing their candidate pipeline flow from 2 interviews per week to 10 per week.
  • In a thirty-day head-to-head test of person vs machine sourcing, the Upsider platform produced four times more candidates than any of the human recruiters in the test.
  • A SaaS company maximized their recruiting efficiency with the Upsider platform, increasing their candidate conversion rate 5x with the use of more data-driven messaging and automation.

Time, experience, learnings, insights. Two years is a lifetime in many ways. Upsider has come a long way and we are super excited to bring our Recruiting Management System to market. The initial impact has been impressive, and we look forward to helping more companies increase the efficiency and predictability of their recruiting efforts. 

Get More Information

If you’d like to see how Upsider can impact your recruiting efforts, please schedule a demo.

To learn how Artificial Intelligence is solving the biggest recruiting efficiencies, click here to get a copy of the informative whitepaper “Impact of Artificial Intelligence on Recruiting”. 

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Here is a story of how one superstar candidate who sold pharmaceuticals made the transition into a different role, overcame all objections before we could make them, and ended up getting hired by a sales manager who would never consider someone with her background.

Before working as a Talent Parter at Upsider, I recruited for a Consumer Packaged Goods (CPG) company where we hired Territory Sales Managers. For context, they sold product into brick and mortar locations. We had an opening in Eugene, OR, and I remember my hiring manager explicitly telling me on our intake call, “I don’t usually interview pharmaceutical sales reps”. Selling into pristine doctor’s offices with air conditioning and nurses walking around in scrubs was not the same environment as run down retail stores with bullet proof glass. The environment and products were on complete opposite spectrums.

So, when I came across a resume for a “National Award Winning Medical Sales Professional” who spent her entire career in pharmaceutical sales, I was hesitant. But, her accomplishments and numbers spoke for themselves, so I thought it would be worth a phone call.

Boy did she WOW me.

On our first phone interview, she demonstrated all the desirable soft skills such as visible displays of excitement and clearly communicating specific examples of her accomplishments and work history. She used the word “fun” way too many times, enough to get the point across.

But what really differentiated her from any other salesperson I’ve interviewed before and what sealed the deal for me was when she told me that before our phone interview, for 2 hours, she had driven around town visiting several local retail shops to see to see where we had distribution, spoke with the business owners about what determined price points and display space, and even bought a few of our products to see what the packaging was like. (Did I mention she didn’t even use our product?)

Needless to say, she carried that momentum into the rest of the interview. Throughout each step of the process, she wrote personalized notes to each interviewer explaining her key takeaways, reaffirming how she could contribute to our success, and thanking us all for our time. She even CC’ed the hiring team, including the hiring manager’s superior on an e-mail that pointed out qualities about the hiring manager that made him a desirable person to work under and learn from. People love genuine compliments.

The research she put into our company and products differentiated her, making her far more desirable than candidates even with relevant experience. The icing on the cake — after she was hired, she sent me a handwritten card.

Talk about building relationships. Every step of the way, she went above and beyond to stand out as the best salesperson I’ve ever interviewed.

Are you looking for a new job or know someone who is? Share these 5 tips with them on how to have the perfect interview.


1) Smile and Dial

Trust me. A recruiter can tell the difference between someone who is beaming with excitement versus someone who is sighing on the other end of the phone like it’s the end of a long day. Even if it is a bad day, suck it up. You have to sell yourself in an interview like you’re selling a product to a prospect.

2) Quantify your accomplishments and contributions

Anyone who watches Shark Tank understands that an investment rarely happens unless the financials make sense. My star candidate was a top performer so she wasn’t afraid to mention her numbers. 167% in 2015, 140% in 2014, 155% in 2013…. need she say more?

3) Use Stories

Maybe you’re not an exceptional performer or you sell Galaxy Note 7’s so you haven’t hit any of your goals. You need to use stories to explain why things did or didn’t go your way. She told an awesome story about how she managed to wiggle in the back door of a client and had a doctor throw a shoe at her, yet she still somehow managed to close the sale 10 minutes later. Make people like you, believe in you, and relate to you, especially if you don’t have the results to prove it.

4) Prove you can do the job before you get the job (especially if you’re changing industries)

Hiring managers, as my founder Drew Koloski sometimes says, can have incestuous hiring tendencies, only speaking with candidates who have relevant experience. It’s easy to prove you can do the job you are interviewing for if you have done it before. For someone looking to change industries, you need to research and hustle.

Do a pre-interview project. For my star candidate, that meant buying our product, pitching the idea to the retailers, and selling the concept. If you’re a salesperson in HRTech trying to break into MarTech, go onto the companies website, create a presentation of their product, and reach out to potential clients. I guarantee if you walk into your interview with 3 potential companies interested in buying their product, you’re chances of landing the job will skyrocket from “lost in the abyss of resumes” to “negotiating a 30% raise”.

5) Be likable

People want to work with people they can sit with 10 hours a day. After her last interview, our star candidate praised the hiring manager and CC’ed his boss. A little flattery goes a long way. After I got my own handwritten note, all of a sudden I wanted to move to Eugene, OR.


Daniel Ahn is currently a Talent Partner here at Upsider and helps salespeople use data to better understand and advance their career.  To learn more and get connected with Dan – visit our home page.

Watch Fifty Shades Darker (2017) Full Movie Online Streaming Online and Download

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Picture yourself as a hotshot Account Executive with three years of selling experience in your first sales job.

You are selling data-driven marketing software as a service (SaaS) to businesses.  You earn a $70,000 base salary and made about $160,000 all in this past year. Not too shabby for 3 years of sales experience (mom was so proud over the holidays). Your Average Order Value (AOV) is $18,000. Sales Cycle, only 38 days.  You hit over 125% of your goal the last two years since you graduated from the Sales Development Rep (SDR) program.  You doubled down early on and took a “blue-collar” approach by applying a tireless work ethic to prospecting.  You still use the skills you learned early on and continue to grind.  You cold prospect systematically, network, you are a leader, are creative – whatever it takes.  Your sales career is off to a fast start!

Now – Fast Forward to 2020. 

Trump is campaigning (and still tweeting…) for a second term, wow did that go fast! Life is good because you leveraged your sales metrics via Upsider to finally landed your first true Enterprise Sales Director role at a big time company. You start right away, congrats! You are excited. Big time deal sizes, challenging sales cycles, C-level decision makers, a legit expense account. Onward and upward, baby!

Start 2017 By Measuring Up to The Best Tech, SaaS & AdTech Sales Jobs in NYC.
Get Started by Entering Your Sales Metrics on our homepage

Your First day

After a 17 minute Hyperloop from 217 miles away, you walk in the door to your new office on your first day feeling confident, if not a little cocky.  Your awesome new company has a powerful brand, hot product and has invested heavily in the latest and greatest in sales development and inbound marketing.  First up? Sales team orientation. You put on your standard issue Virtual Reality (VR) headset for the new hire presentation and pass out some virtual fist bumps to your new teammates in other locations.  You are all sitting in a virtual tent at a virtual base camp on virtual Mount Everest. Nice touch, inspiring!

Continue reading AI or Bots Won’t Make You $200,000+ in Your Next Sales Job

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Have you ever wondered how sales job opportunities “open up”?  Is it because someone left the company? Did someone not hit their number and get fired? Does it come from the budget surplus of a sudden growth initiative? Maybe there was extra budget left over in Q4, and management is saying “it’s got to go somewhere!” or the hiring manager has the “use it or lose it” mentality.

Continue reading Your Dream Sales Job Is Probably Not Open

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typewriter_upsiderQ4 is coming soon, are you ready? It’s a critical time of year if you are in sales and it’s important to roll into October full steam ahead. Sure you can make more calls, send more emails – just do more, right? Alternatively – you can try to work smarter, and do something to differentiate yourself. What are you doing to start adding your knowledge or relevant personal experience to your prospecting to help convert outreach and move the sales cycle faster? Continue reading Q4 is Coming. Salespeople Write Something Immediately.

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After a lot of speculation, leaks and poorly kept secrets Apple announced the newiPhone 7 today. The big reveal: it doesn’t include the familiar analog headphone jack. There’s already much controversy and opinion on this potentially bold, if not risky, move for Apple. Not that they haven’t done it before.

Innovation always comes with risk. But sometimes it takes much longer than you may think for mainstream adoption.  It took about 3 years for the New York Times to mention the Wright brothers after their first flight — and that was for the accomplishment of enabling humans to fly.

The ways in which salespeople discover jobs and employers find salespeople is in need of the some serious innovation, particularly in regards to “the headphone jack of sales recruiting”: the resume.

James Martin/CNET

James Martin/CNET

Continue reading Killing the Headphone Jack for Sales Hiring

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If you are a salesperson starting to sense that a big career move is on the horizon, you might be asking yourself, “When is the best time to change sales jobs?” This is a common question we hear from our community of data driven, high performing salespeople at Upsider.

NFL Quarterback Ryan Fitzpatrick was coming off a career year on the veteran’s minimum salary, and recently signed his 2016 contract with the New York Jets on the first day of training camp after a long, drawn out negotiation. If Fitzpatrick held out any longer, he would have missed his ramp up period to get ready for the regular season. Because he understood the value of starting at the right time, he decided to compromise on the up front contract value to get the start he needs. This will help his performance, and if he hits the right incentives and bonuses, he’ll make up the difference and then some.

Ryan Fitzpatrick signs with the New York Jets on the first day of training camp.

Ryan Fitzpatrick signs with the New York Jets on the first day of training camp.

Like with Fitzpatrick, timing matters for salespeople having a “career year.” Top salespeople with a consistent track record of over-performance face a big risk and have more to lose than most others when deciding to change jobs. When the consistent commission dollars are at stake, lowering your risk profile so you can feel confident enough to go for the big time career growth and an upside payday at a new company is essential. Continue reading Why September Is the Best Time to Start a New Sales Job

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Sales Data upsider

Using data in your day to day sales role is the new normal, but have you thought about how to store, access and use it to help make sense of your sales career? Do you routinely use it to measure and analyze your personal sales success on a weekly, quarterly and annual basis? Do you compare notes with teammates? Salespeople at other companies? Is that enough data for you to feel good about it as a reference point? Do you happen to have a safe, organized place to store your data as you shift from company to company? Is it in a spreadsheet? A little black book? How about that old Windows machine sitting in your closet? You may be data driven when it comes to plugging in to your sales organization’s sales stack, but with a demanding job, accurately collecting and analyzing data to measure your career growth and upside can prove challenging. Continue reading Is Your Sales Job More Data Driven Than Your Sales Career?

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If you are the #1 or #2 ranked salesperson at your company, do often wonder, “could I be making more money somewhere else?” and “who are the companies that could offer me the right upside career opportunity?” What would it take to offset the risk of leaving your company where you are the top dog? Do you know when it’s time to leave, or when to jump at a great opportunity? How do you approach finding the absolute best opportunity? Continue reading 5 Tips for High Performing Salespeople Who Hate Searching for Jobs

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Solid Sales Reads is featured on President’s Club – our Medium Publication. 


John Paul Narowski talks about the value of asking for referrals and explains that timing is everything in The Best Time to Ask For Referrals.

Inside the Deal

Tal Vinnik informs us that B2B Sales Cycles are getting longer and reassures that this is a good thing for salespeople in B2B Sales Cycles are Getting Longer — And That’s Okay.

Russ Heddleston gives us 4 top notch pointers to make sure we learn from Nike’s big time deal blunder in What Every Seller Should Learn from Nike’s $14bn Steph Curry Mistake. -via Sales Hacker

Mind Over Matter

Daniel Meek is kind enough to share the most common trends he sees in great sales hires over time in Lessons Learned Interviewing 1,000 Sales Candidates.

Jermaine Edwards explains why making some time to think can provide a great personal ROI for your sales in 5 ways better thinking will transform your sales.

Chris Spurvey shares the what it takes habitually, to be a high performing salesperson in Seven Habits of Highly Effective Salespeople.

Thank you for reading!

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Have you written or read something sales related you think is interesting? We’d love to check it out — send us a note at


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