Sales Trainer at BigTime Software, Inc.

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BigTime is the engine behind the greatest consulting firms on the planet, delivering back-office time/budgeting and invoicing to over 2,000 firms worldwide and tracking over $3 billion in billable time each year.  Our flagship product is a SaaS-based system that is custom-built for the professional services industry.  BigTime is a PE-backed company based in Chicago committed to helping clients run professional teams more efficiently, unlocking potential revenue and improving profitability.

If you love what you do, and want to work in a fast-paced, entrepreneurial environment that will challenge you to do your best, then check us out!

BigTime Software is looking to add an in-house Sales Trainer to build and deliver BigTime’s Sales Curriculum. Reporting to the SVP of Sales,  this individual will be focused on developing and delivering engaging, results-driven sales training to increase the effectiveness of the sales team while increasing the speed at which our team ramps to full productivity.  This individual will not only be an integral part of the sales training and onboarding of new reps as we scale the team, they will also provide skill gap analysis and provide ongoing training for the existing reps within the Sales Organization.  This is a key role as we continue to grow and scale our sales team and will have a direct and critical impact on revenue growth and target obtainment.  If you are someone who is driven by making an impact and seeing the results of your work, this is an incredible opportunity to join a team where your work is highly valued. 

What you will be responsible for:

  • Partner with the SVP of Sales to outline and execute on the key training initiatives and priorities
  • Become an expert on the Sales Organizations inner workings including procedures, policies, best practices, systems and tools to incorporate into training initiatives and priorities setting. 
  • Develop, create, deliver, measure, and reinforce ongoing training activities to ensure continuous learning and development opportunities for Sales team members across all levels
  • Develop and deliver all sales training and onboarding for all new sales employees 
  • Work in step with the People team to develop a competency framework for hiring, training and the ongoing performance management of the sales team. 
  • Manage other projects within the sales training and enablement programs as identified and assigned
  • Work cross functionally and collaboratively with all departments across the organization to ensure knowledge sharing and alignment with other teams 
  • Identify skill gaps and opportunities for improvement and ongoing training needs across the sales organization
  • Provide regular follow-up training modules to deepen product and industry knowledge across teams.
  • Collaborate with the product team on all product updates and feature releases in order to successfully roll out applicable training across all teams 

In Order to qualify, you should have: 

  • 2+ years of experience in sales enablement or sales training, including new hire onboarding, and ongoing training
  • 2+ years sales experience with demonstrated success as a B2B SaaS Account Executive or Account management role
  • Bachelor's Degree required
  • Familiar with sales specific training programs, consultative sales preferred
  • Experience with Salesforce or other CRM applications
  • Experience with creating and delivering engaging content for sales enablement
  • Be results oriented and focused on measuring the success and effectiveness of the sales training program
  • Strong interpersonal communication skills - must be able to engage the room you are training; driving thoughtful and engaging discussions
  • Must be results oriented and data driven and meticulous with tracking the effectiveness and results of the trainings provided
  • Passionate about making an impact on those coming through your trainings (both new hire and ongoing trainings) and the impact that has on the growth of BigTime
  • Role is temporarily remote and will eventually transition back to our downtown Chicago office

Working at BigTime has its benefits!

  • Competitive salary and bonus potential
  • Company paid benefits, including medical, dental, vision, disability and life insurance
  • 401k with company match
  • Paid Parental Leave
  • Generous time off and paid company holidays
  • Company provided latest technology & software tools
  • Weekly Lunch Credit via DoorDash and company paid DashPass (free unlimited delivery)
  • While the role is based in Chicago, we offer a Flexible Work Environment with opportunity to work remotely
  • Fresh fruit, snacks, cold brew coffee/tea, soda and La Croix
  • Great, convenient downtown / loop location (While we are still working remotely due to COVID, we feel this is worth highlighting)

Applicants must be authorized to work in the U.S.  BigTime Software, Inc. is proud to be an Equal Opportunity Employer

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability, protected veteran status, or any other characteristic protected by law.

Your Right to Work - In compliance with federal law, all persons hired will be required to verify identity and eligibility to work in the United States and to complete the required employment eligibility verification document form upon hire.


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Technology we use

  • Engineering
  • Product
  • Sales & Marketing
    • .NETLanguages
    • C#Languages
    • JavascriptLanguages
    • SqlLanguages
    • AngularJSFrameworks
    • MongoDBDatabases
    • Google AnalyticsAnalytics
    • IllustratorDesign
    • InVisionDesign
    • PhotoshopDesign
    • BasecampManagement
    • WordpressCMS
    • HubSpotCRM
    • SalesforceCRM


We're centrally located in The Loop close to public transportation and steps away from many many restaurants.

What are BigTime Software, Inc. Perks + Benefits

BigTime Software, Inc. Benefits Overview

BigTime Software is one of the region's best companies, serving Chicagoland communities in Illinois. Our team enjoys training programs, a fantastic culture, and opportunities for advancement, which are company-wide focuses to help you grow both personally and professionally. We're interested in helping your career and adding to your resume because we know that happy employees lead to happier customers!

- Opportunities for Advancement
- Company Provided Latest Technology & Software Tools
- Great, Convenient Downtown/Loop Location
- Company Paid Benefits
- Weekly Catered Lunch and Whole Company Meeting
- Minimum of 11 Paid Holidays
- 401(k) Savings Plan with a match
- Snacks, Cold Brew, La Croix, Bubbly and More

Volunteer in local community
Friends outside of work
Eat lunch together
Intracompany committees
Our Culture Committee has four sub-committees: - Diversity and Inclusion - Community Involvement - Wellness - Social
Daily sync
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Open office floor plan
Dedicated Diversity/Inclusion Staff
Unconscious bias training
Diversity manifesto
Diversity Employee Resource Groups
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Onsite Gym
Retirement & Stock Options Benefits
401(K) Matching
Performance Bonus
Match charitable contributions
Child Care & Parental Leave Benefits
Generous Parental Leave
We provide up to 12 weeks of parental leave: 6 weeks for bonding time and up to 6 weeks for medical leave.
Remote Work Program
Family Medical Leave
Vacation & Time Off Benefits
Generous PTO
Paid Holidays
Paid Sick Days
Perks & Discounts
Casual Dress
Commuter Benefits
Company Outings
Stocked Kitchen
Some Meals Provided
Happy Hours
Happy hours are hosted at the team's discretion.
Professional Development Benefits
Job Training & Conferences
BigTime offers employees professional development opportunities like the ability to attend job-related conferences and seminars.
Diversity Program
Lunch and learns
BigTime hosts lunch and learn meetings weekly.
Cross functional training encouraged
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