Author's Posts

Last week we sat down with Peter Phelan, the co-founder and CEO of ValuesCulture, to discuss the cross section of building winning cultures and how to best leverage data within an HR organization. Peter has a wealth of experience, spending over 20 years working with leading companies like Shutterstock, MediaMath, Bloomberg, Publicis Groupe, and WPP. We were excited to hear his thoughts on culture, data, and how HR teams are innovating.

 Tell us about ValuesCulture. Who do you work with and how do you help them?

I founded ValuesCulture to provide Culture Doctor services to growing Silicon Alley companies who want to maintain a healthy and resilient organizational culture. Like any good doctor, the first goal is to leverage experience and specialist training to diagnose objectively. Then, with a good desk-side manner, we provide accurate prescriptions on how to promote system health.

 How does a company create a winning culture?

In my experience – first knowing in very specific terms what winning looks like is step one. If you’re on the right track with this “What & Why” you should be able to capture it in a handful of words. After that, it’s incredibly important to establish a shared understanding of how this team will go about achieving the win together. Don’t make the mistake of throwing together some nice-sounding values and bring them down from the mountain to the team. If they don’t ring true to the team – you’ll cause cognitive dissonance and hurt trust. Discretionary effort might be the next victim. When ValuesCulture does a Values Definition Exercise it’s very data driven with lots of stakeholders ranking organizational competencies in a very structured way. We leverage any data we can access from employee surveys, client-facing brand positioning, and we have leaders use style assessment tools. We’re looking to get at making promises in values that the organization is wired to keep in a very fundamental, sometimes even subconscious, ways.

How should a company evaluate the strength of their culture?

We’re big believers in the power of data. Anonymous employee surveys are a great way to tap into how aligned a team is on “the way we get things done” (which I feel is great shorthand for organizational culture). There are lots of solid off-the-shelf tools for this purpose – many of which borrow from the classic Gallup 12 engagement questions.

Who within the company drives culture?

While everyone has the power to influence a culture in some way – those in leadership positions have an outside impact on setting the culture – none more so than the CEO. Where the People Team can be very impactful is in leveraging their expertise on culture to partner with leaders, so they’re tuned in to their impact on the culture and curate their signals accordingly. Great people leaders can guide leadership teams toward conscious competence in curating positive cultures that inspire discretionary effort.

How is it different between a 25-person company and a 500-person company?

Well, the stakes keep on getting higher. If a CEO unwittingly sends the wrong cultural message with 25 it might be possible to clean things up by doing 1:1 time with everyone and rebuilding trust. It’s harder to recover when you’ve disappointed/demotivated 500 people.

Can organizations use data-driven approaches to measure culture?

To know your culture well enough to help it scale and evolve, I believe a data-driven approach is the only way to curate a culture.

How do you source candidates with culture in mind?

“Cultural Fit” has been definitely weaponized in unhealthy ways. A candidate might be deemed to be “not a cultural fit” if they’re, for example, too old for the manager’s comfort level. So, to avoid behavior like that, it’s important to have a very clear sense of behavioral competencies that lead to good outcomes in your organization. Then, showcase that “clear sense of organizational self” in all of your job specs and employer branding. Then in every community where you spread the word about your organization – you’ll filter in and out talent effectively by showcasing your organization’s personality.

How do you interview for cultural fit?

If you do consistent structured behavioral interviewing that tests for values alignment (on values you’ve identified in an objective data-driven alignment process) by drawing out multiple examples of situations/scenarios – you won’t go far wrong!

How will technology change the way HR professionals do their jobs?

In a way, for the in-house People Pro, it’ll remain quite a human profession in that what’s routine or non-core to your business will be automated or outsourced.

What impact do you think Artificial Intelligence will have in the world of HR?

Well, Recruiting Coordinator may not be a job in five years. But, more significantly, I think that we’re about to enter a transformative time where data science and people analytics will be part of every People Team and AI will be an important tool. People are your single greatest asset/expense – so using the best tools available to optimize their success is just good business.

3 predictions for the HR industry in 2018?
  1. Data Science will open our eyes to the myriad ways we routinely shoot ourselves in the foot with talent!
  2. Sourcing will be increasingly automated, leveraging AI, for a growing number of roles.
  3. People will be routinely surprised that the person who set up their interview wasn’t a person.
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Over the last few months, we’ve talked with numerous companies of all sizes about their 2018 recruiting strategies and how they’re thinking about Artificial Intelligence (AI). AI is on everyone’s mind, but the industry is early in the process of figuring out how to best implement it across the recruiting function. Like any new transformational technology, there is a lot of speculation around it’s true impact. To help provide some clarity, we’ve highlighted the five most frequently asked questions from those conversations, and provided our perspective based on the last seven months of executing AI-driven recruiting for our clients.


1. How is Artificial Intelligence changing the recruiting function?

Recruiting is, and will continue to be, a mission critical function for companies of all sizes. It isn’t going anywhere. However, this very manually-oriented, time-consuming and expensive process is being disrupted and revolutionized by Artificial Intelligence, which is starting to play a massive role in making the recruiting process more predictive, efficient, and cost-effective.

According to, Artificial intelligence is fast establishing itself as a game-changer in the recruiting process, enabling organizations to more readily find and hire just the right candidate for the job1.

One of the biggest benefits of the advancements in AI and machine learning in recruiting is the improvement in efficiency. Using known data about the role and the business, AI removes massive inefficiencies from the recruiting process. Repetitive tasks can be condensed from weeks to minutes, allowing employees to allocate more time to higher value tasks.

Being able to crunch data in real-time allows recruiting teams to be more strategic by creating forecasts of time and level of effort required to hit hiring timelines. This allows recruiters to spend time on higher value activities like personalization, relationship building, and candidate nurturing.

Costs savings are derived through increased productivity per recruiter, less reliance on staffing firms, and other lower ROI-based spend.

In LinkedIn’s recently released Global Recruiting Trends 20182 survey, it identifies AI as one of the four trends that will shape the future of recruiting. Companies who move first will have a significant advantage over their competitors in the war for talent.


2. What are the requirements to implement an AI and data-driven system?

LinkedIn’s 2018 survey outlined the areas where AI will have the biggest impact on recruiting. These include repetitive tasks like candidate sourcing, resume collection/parsing and nurture marketing2. Recruiting teams should start applying AI to these activities, as they will provide the biggest positive impact to the process and fastest ROI.

In a recent blog post, we outlined the keys to getting started with AI. The actual requirements to get started using AI are very minimal. Three key steps to get underway:

  1. Gather the targeting parameters. A tool like Upsider leverages information you already have available, such as job requirements and metrics about the role. This includes the information hiring managers and recruiters are tracking on a regular basis. For example, for technical hires, data scientist, 10+ years experience, salary range $x-y, target hire date, etc.; or in a sales role, revenue goals, average order value, close rates, territory, and resulting comp package. Collect those metrics about the role and overall company business objectives.
  1. Run the facts about the role and business through the AI engine, which will analyze hundreds of variables across millions of companies. The AI engine will immediately identify the total pool of candidates who align with the role metrics. With the pool of candidates identified, recruiters can select any number of prospects with whom to start the engagement process with. 
  1. Execute outreach nurture messaging to connect with candidates, delivering relevant messages at the right time as they consider new career opportunities. Sell the role, highlight how the job will further career goals, eliminate objections. Deliver messages across email and social channels.


3. In light of the buzz around AI replacing jobs, how do I get my team to embrace AI tools?

It’s safe to say that recruiters may not love the tedious process of sourcing candidates, asking their hiring manager for the dreaded “list of companies” to target, or searching resume databases for days and weeks to find a list of reasonable candidates.

AI eliminates these manual tasks and allows the recruiter to spend their time on strategic activities like creating a more relevant outreach program, executing high-value candidate nurturing, doing deeper research on candidate background, and increasing their bandwidth to take on more roles. AI drives massive productivity gains.

We have experienced the productivity gains first hand. During our development process building the Upsider platform, we worked with a few dozen clients in full-service recruiting engagements. Most of these relationships started before the platform was ready for testing, so our recruiters transitioned from traditional recruiting tactics to AI automation. Once they began the AI assisted recruiting process, they immediately became 5x more productive. We detailed the process in a recent blog post.

AI won’t replace recruiting jobs. It will make those jobs better, eliminating the monotonous aspects, freeing up the recruiter to work on the more rewarding facets of the role – helping the hiring manager find great candidates (quickly) and assisting the best of those candidates to take new roles that help their careers. A win-win (and win for the recruiter).


4. How will AI impact my relationship with hiring managers?

We spent a lot of time with hiring managers while building the Upsider product. One of the biggest complaints we heard from their perspective: “Recruiting is like a black box. We submit our requirements, it goes dark, and then we get asked to review interested candidates. If there isn’t enough candidate flow, we typically do not know why, and we don’t hear much feedback from the recruiter during the process.”

AI and a data-driven platform can have a significant impact on this recruiter/hiring manager relationship. Because AI can analyze millions of candidates across hundreds of variables, it arms recruiting teams with deep data insights to impact the search, from requirements development through the recruiting process.

Once this recruiting process is underway, the AI system returns predictable conversion rates and timelines, enabling recruiters to communicate to hiring managers the number of candidates available for outreach, as well as the expected follow-on conversion rates: how many responses expected, number of screening calls that will be made, the size of the qualified candidate pool, and finally — the hire, and as important, how long that role will take to fill. Being able to present the required candidate pool size and the “projected role fill date” is an effective way to manage expectations.

This results in better predictability and accurate forecasts for candidate fulfillment, which is critical for managing the recruiter/hiring manager relationship. The black box is eliminated. Clearly, AI will have a major positive impact on this critical relationship.


5. How is ROI measured with AI-based tools?

AI introduces tools that make the recruiting process significantly more efficient. Recruiters become more impactful, productive, and strategic, allowing them to spend time on higher value activities like personalization, relationship building, and candidate nurturing.  Costs savings are derived through increased productivity per recruiter, less reliance on broad based candidate acquisition spending, and other lower ROI-based spend. AI’s impact can be tangibly measured throughout the recruiting process.

Key performance indicators include:

  • Time-to-hire
  • Conversion rates through the recruiting stages
  • Reduction in candidate-generation advertising spend
  • Overall cost per hire
  • Employee retention rates


Find out more about AI and Recruiting

If you’re interested in learning more about how other companies are taking advantage of AI in their recruiting process, and learn how you can use AI, you can easily contact us and/or schedule a demo at 


  1. Note. From “How AI is revolutionizing recruiting and hiring,” posted by CIO | September 1, 2017
  2. Note. From “2018 Global Recruiting Trends” posted by LinkedIn Talent Solutions | January, 2018
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This past June I graduated from Princeton University and entered the business world. I interned in HR/Recruiting in summers past, and while I liked it, I learned pretty quickly that the space had a lot of room for innovation. So, I went into my job search with the goal of finding an innovative role in talent management or HR.

Enter Upsider: interviews with Upsider were informative and exciting – Upsider is using Artificial Intelligence (AI) to automate the most time-consuming parts of the sourcing process, and it clicked: this was the innovation that the recruiting space needed, and what I wanted to be a part of.

Old School

When I first joined Upsider, my time was spent as a recruiter, executing with traditional recruiting tactics – browsing resume databases, sourcing on social networks, etc. – for a group of full-service clients. The job requirements and hiring timelines were not based on data, but on an internal, client-imposed set of milestones, i.e. “Need a new salesperson to start next month in Phoenix!…”.  Forecasting candidate pools, conversion rates, and hiring timelines was complete guesswork. I spent most of my time just trying to find the right people to message, and it left little time for the strategic work of personalization and nurturing. Really, the whole process was pretty inefficient.

New School

My timing to join Upsider aligned well with their timeline to start internally testing their new AI recruiting tools. Before long, I transitioned to using the Upsider Recruiting Management System (RMS), and that was a huge game changer. Suddenly, my time was super optimized; when we took on a new role, instead of spending weeks trying to identify a target group of candidates, I was immediately presented with a list of candidates that aligned with the business and the specifics of the role. Additionally, there were data-driven insights that I could use in my outreach to the candidates. I was told by candidates I worked with that the data insights were also helpful to them in evaluating whether or not they wanted to learn more about the role and the employer.

Upsider’s AI tools allowed me to focus on high-value activities, like more personalized messages and establishing relationships with the candidates. I was able to spend more time on the things that mattered, instead of using it all up researching and looking through the haystack of profiles. Using our product, I saw my productivity metrics increased by 5x in the number of candidates calls I was having per week, and that continued on through the rest of my recruiting funnel (candidate submittals, interviews, etc.).

Example of our AI in Action:

We received a call from a client with an urgent need to backfill for someone who unexpectedly resigned. They let us know during this call that they’d reached out to four recruiting agencies to work on the role as well. Through the use of our RMS, we were able to submit eight well-matched candidates by the end of that week, while the four agencies submitted just one person. And that’s not one each, but one total!

AI is the Future, and the Future is Now

In 2017, AI was (and probably will continue to be) ubiquitous– it’s the subject of countless articles and the foundation of numerous startups, and while I’d heard and read a lot about how AI would impact industries and jobs, I never directly experienced AI in a specific application that impacted my workflow until I got to Upsider. While everyone talks about AI taking jobs, this is an application that makes me more valuable. My productivity measurably increased, and I was able to eliminate the monotonous aspects of recruiting – if this is the future, I am so in!

I know you recruiters out there would love to get in on this awesome technology, and that’s the best part! We’ve built our RMS to be accessible to any company and/or recruiter. If you’d like to see a demo, feel free to visit us here:

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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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