Sales Enablement Manager, SDR at TripActions

| Chicago
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We are seeking a highly motivated and energetic SDR Sales Training and Enablement professional to join our Sales Enablement team to help drive onboarding, coaching and training for our new and existing Sales Development Representatives. In this individual contributor role, you will work closely with the SDR leadership team as a business partner to understand their biggest priorities and challenges, gather quantitative and qualitative data (through informal interviews), and deliver programs that drive impact across the SDR org. You will also build, plan, schedule, coordinate and deliver the in-person and online Sales Academy experience to new SDR hires. Other responsibilities include shadowing SDR live calls, listening to call recordings, and providing actionable feedback to frontline managers and representatives. Finally, you will create content and curriculums and administer tools that impact our entire SDR organization.

The ideal candidate is passionate about coaching, training, and crafting curriculums that accelerate the growth of new hires and ensures the success of our sales teams. This is an amazing opportunity to have a significant impact on the time to ramp of our new SDR hires, as well as to increase overall per-rep productivity.

What You'll Do:

  • Partner with SDR Leadership team (VPs, Directors and Managers) to understand the SDR organizations’ goals, priorities, and challenges
  • Establish key performance indicators to track sales training program efficacy; work with SDR leadership team, vendors and Sales Operations team to further develop and maintain KPIs (ie. time to first meeting, time to quota, % of SDRs at Quota, stage-by-stage conversion), dashboards, and reporting to drive curriculum improvements.
  • Conduct quantitative and qualitative analysis (through informal interviews, call recording reviews, etc.) to uncover SDRs’ biggest hurdles and roadblocks
  • Create content, training programs and curriculums to address these roadblocks
  • Build coaching guides for SDR managers to reinforce learnings post-training
  • Record, measure, and report results to SDR and Sales Leadership team
  • Deliver one to four-week onboarding and training programs comprised of in-classroom training, self-paced on-demand learning, peer mentorship program, discovery certification
  • Provide hands-on training through call shadowing and by listening to call recordings, and give feedback directly to managers and reps
  • Enable sales managers to ensure that key training concepts are continually reinforced post-training
  • Inspire and educate our new SDR hires, integrating the building blocks for their role-specific learning path
  • Produce interactive exercises to drive high level of engagement and knowledge retainment
  • Create and administer quizzes and exams to measure learning and understanding of key concepts
  • Collaborate to react quickly to any decrease in metrics, putting a plan into place with stakeholders to make immediate improvements.
  • Partner with SDR Leadership to identify knowledge and skill gaps across the SDR team and roll out targeted programs
  • Work closely with our key vendors to ensure that our field teams are getting maximum value from their solutions

 What We're Looking For:

  • 2+ years of SaaS sales experience as a top performer and/or minimum of 1+ years of sales enablement, sales training and/or consulting experience
  • Familiarity with formal sales methodologies such as Challenger Sales, Sandler Sales, and SPIN preferred
  • Experience with Learning Management Systems
  • Familiarity with sales tools such as Guru,, Highspot, Zoominfo, Salesloft, Outreach, Salesforce
  • BA or BS in Business Administration, Psychology, Advertising, Communications, Journalism, Political Science, Liberal Arts, History and/or equivalent formal training or experience
  • Proven track record in creating, delivering, and training successfully with measurable results in fast paced environments
  • Strong ability to represent concepts, as well as summarize and communicate complex ideas into curriculum with a strong sense of how sales professionals think, operate and absorb training
  • Passion for coaching and educating others
  • Strong process and analytical skills to identify inefficiencies and create improvements
  • Ability to thrive in a dynamic and changing environment
  • You have a collaborative working style, experience working across the company with teams of varied size to achieve common goals
  • Experience in fast-growth, SaaS startup environments highly desired
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Technology we use

  • Product
  • Sales & Marketing
    • AsanaManagement
    • SalesforceCRM
    • salesloftLead Gen


A stylish neighborhood near the Mag Mile, River North is home to 400 tech startups and some of the most popular dinner and drink places in Chicago!

An Insider's view of TripActions

What’s the vibe like in the office?

Everyone comes into the office with a ton of energy every morning ready to make an impact. Because we are still small, there are constantly opportunities to collaborate and learn from one another. We also make sure to balance time outside of the office to have some fun while strengthening the relationships within our teams.


Sales Development Manager

What does your typical day look like?

As an AE there is no such thing as a typical day. I try to block 2.5 hours a day for prospecting and then prep for upcoming demo’s/calls. I to do a ton of research on the company to go in as prepared as possible. My goal is to understand what they do, why they love their company and how TripActions might help them with making travel stress-free.


Commercial Account Executive

How does the company support your career growth?

TripActions provides me with a clear understanding and support to get to the next step in my career. After expressing interest in being a cultural pillar in our new Chicago office, I worked with my manager and director to develop a plan. Being able to directly communicate with management has given me the opportunity to grow at an amazing company.


Sales Development Representative

How do you make yourself accessible to the rest of the team?

We don’t have an ‘open door’ policy because if you’re an accessible leader, there is no reason for a door in the first place.


Director of Sales

What projects are you most excited about?

Frankly, one of the best things about working at TripActions is the sheer depth and breadth of exposure that people get to teams and projects. Everyone is humble and accessible and there are few if any walled gardens. Right now I'm looking forward to our team hackathon as well as the launch of better direct connectivity with air carriers.


Director of Product Marketing

What are TripActions Perks + Benefits

Volunteer in local community
Partners with Nonprofits
Friends outside of work
Eat lunch together
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Pair programming
Open office floor plan
Dedicated Diversity/Inclusion Staff
Highly diverse management team
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Pet Insurance
Wellness Programs
Retirement & Stock Options Benefits
401(K) Matching
Company Equity
Performance Bonus
Child Care & Parental Leave Benefits
Generous Parental Leave
Family Medical Leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Holidays
Paid Sick Days
Perks & Discounts
Casual Dress
Commuter Benefits
Company Outings
Free Daily Meals
Some Meals Provided
Happy Hours
Pet Friendly
Fitness Subsidies
Professional Development Benefits
Diversity Program
Lunch and learns
Cross functional training encouraged
Promote from within
Mentorship program