Trainer, Sales Development

| Chicago

Hireology’s technology empowers businesses to build great teams. Over the last nine years, we’ve grown from a startup to a market-leading organization with over 195 team members, and we’ve created an award-winning culture that makes this company an amazing place to work.

To enable the continued growth of our sales team, we are looking for a Trainer, Sales Development. It is your mission to ensure our sales team members are set up for success in achieving quota goals at Hireology. You will be responsible for increasing sales productivity and efficiency by developing the sales skills of our team. As we identify opportunities for education, you will help build new training content and ensure all of the training materials are ready to be delivered. From there, you’ll deploy your coaching tactics and assess progress.

We expect that you will thrive in a fast-paced environment and bring your proven sales experience to our Training team. You will report into our Manager of Sales and Customer Success Training.

As our Trainer, Sales Development, you’ll be responsible for:

  • Delivering training content to improve rep sales skill, including topics like sales process, discovery, objection handling, and reviewing value
  • Facilitating and managing our New Hire Orientation program and making enhancements, iterations as needed
  • Executing training programs, bootcamps and workshops to further skill growth in large and small group sessions
  • Shadowing and coaching our team members with assessment tools ready
  • Partnering closely with Sales Operations to ensure mastery of sales tools and execute on training needs
  • Partnering closely with Marketing on Sales enablement materials 

So what kind of person are we looking for in this role? We have a pretty unique culture here at Hireology, and the person who will be successful in this role will be:

  • Proven track record selling: You’ve been in the field and you have a background in sales methodologies and tactics
  • Fulfilled watching team members grow: You are motivated by the success of others
  • Strong presenter: Bringing high energy and thriving in front of a group
  • Agile thinker: Able to create new ideas, try new things, and move quickly to help our team improve
  • Able to grow with Hireology: Capable of growing as our company grows with the ability to lead others
  • A true culture fit: Highly optimistic yet pragmatic attitude and contribute meaningfully to Hireology’s culture

Okay, we’ve laid out what the job is - now are you qualified? Below are the qualifications we’re looking for in a Trainer, Sales Development. Also, we want a chance to get to know why you applied, so please include a cover letter.

  • 1-2+ years of Sales experience at a B2B software company with a demonstrated record of success
  • 1+ years of internal Training experience with skill evaluations, assessments or training program development
  • Bachelor's Degree
  • Experience using Salesforce or other sales enablement tools preferred
  • Excellence in communication skills: written, verbal, and presentation
  • Strong project management skills with demonstrated ability to manage multiple projects or priorities at once.

So what can you expect after you apply? You will:

  • Take a brief true/false survey. Be sure to check your email after you apply.
  • Have a phone conversation with someone on our Recruiting team. This is a high-level conversation about you, but also a good opportunity for you to learn more about us.
  • Meet with our Sales and Training team to discuss how your past experiences will enable you to be successful in this role. Be prepared to walk us through your sales experience with examples of how you have done it in the past. No homework or on-the-spot assignments. We just want to see how you would make an impact in this role.
  • Take a strategic critical thinking assessment that determines how we can develop you at Hireology.
  • Provide us with some references. We use our automated reference check system for this, so you just give us some names, they fill out a survey, and we are all set.
  • Speak with our Senior Leadership team including our VP of Sales. 
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Technology we use

  • Engineering
    • GolangLanguages
    • RubyLanguages
    • ReactLibraries
    • Ruby on RailsFrameworks


Unbeatable office space in downtown Chicago, with views of the Chicago River and Navy Pier.

What are Hireology Perks + Benefits

Health Insurance & Wellness Benefits
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Onsite Gym
Retirement & Stock Options Benefits
401(K) Matching
Child Care & Parental Leave Benefits
Generous Parental Leave
Flexible Work Schedule
Vacation & Time Off Benefits
Unlimited Vacation Policy
Generous PTO
Paid Volunteer Time
Paid Holidays
Paid Sick Days
Perks & Discounts
Beer on Tap
Casual Dress
Commuter Benefits
Company Outings
Stocked Kitchen
Some Meals Provided
Happy Hours
Recreational Clubs
Professional Development Benefits
Job Training & Conferences
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