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Sales Trainer

WHO WE ARE


SQUIRE is the leading business management system designed for the needs of barbers, shop owners, and their communities. We believe the pursuit of artistry and autonomy should not be restricted by the complexities of running a business. With SQUIRE, we provide custom-branded tools, resources, and guidance to help barbers of all stages and experience levels attract and retain more customers, efficiently manage their shop operations, and increase their revenue.


Founded in 2015, SQUIRE is trusted by barbers in 4,000+ shops in more than a thousand cities around the globe. From streamlined booking and opening new shops to real-time earning dashboards and building lasting customer relationships, SQUIRE supports shop owners in seamlessly bridging the gap between their personal craft and business goals. SQUIRE enables barbers everywhere to unlock their full potential both as artists and as entrepreneurs.


For more information, please visit getsquire.com or download the SQUIRE app from the App or Play Store.

 


SUMMARY

The Sales Trainer will be responsible for overseeing, developing, and managing the onboarding and ongoing training program for our Sales team at SQUIRE. These programs will include both virtual instructor-led and live instructor-led training, as well as eLearning, video, coaching guides, and other enablement assets. This role will work closely with the GTM Enablement team, Revenue Operations, and Sales Leadership to enable the team to perform at its best potential and capacity.


The person who will succeed in this role can work independently, is a problem solver, and is a great collaborator. This position is a fit for anyone that loves the challenge of training sales teams across a variety of skill levels, and pushing everyone to be the best versions of themselves. 


REPORTS TO

Director, GTM Enablement


LOCATION

Austin, TX - Hybrid (minimum 3 days a week in office, but will need to be in office 5 days a week during NHO and needs to be on-site for any training with the ATX-based team)


JOB DUTIES AND RESPONSIBILITIES
  • Revise, optimize, and lead onboarding for Sales new hires, including building out decks, creating engaging activities, and facilitating all sessions
  • Partner with the Strategy & Insights team and Sales Leadership to identify skill or knowledge gaps and create cohort-based training & coaching programs that close those gaps
  • Track sales performance across the field and work to turn C players into B players and B players into A players using real-time coaching, ride-alongs, and deal support on the sales floor 
  • Create enablement packages for ongoing training reinforcement that include multiple learning modes (live, eLearning, reference documentation, reinforcement guides) and use Highspot to surface that content in the flow of work
  • Conduct call reviews regularly to monitor for skill & knowledge gaps
  • Provide additional coaching and feedback as needed for reps at all stages of the sales cycle, in partnership with our sales managers 

The duties and responsibilities outlined above are not a comprehensive list and additional tasks may be assigned from time to time based on business needs.


REQUIREMENTS AND QUALIFICATIONS
  • 1+ years of experience in a Sales Enablement or Training role, working directly with quota-carrying teams OR 2+ years of experience in an Inside Sales or SDR role with heavy cold calling and self-prospecting
  • Familiarity with Sales playbooks, cold call scripts, cadence tools, and other structures that support high-velocity sales motionsFamiliarity with Salesloft, Salesforce, Chili Piper, and Highspot preferred
  • Ability to multi-task and operate under pressure, delivering high-quality work on tight timelines and pivoting as needed
  • Expert communicator who can gather buy-in from key stakeholders and drive change with the Sales team
  • Fast learner with a growth mindset who believes feedback is a gift and gives and receives it in that spirit
  • Ability to be in office minimum 3 days a week and up to 5 days a week when the business requires it (this requirement is not flexible, and ideal candidates for this role must thrive in a sales floor environment)
  • Fluency in Spanish is a plus but not required


WHAT WE OFFER
  • Base Salary ($80K - $90K) + VC ($30K - $40K) for an OTE of $120K
  • New hire stock grant
  • 100% employer paid medical, dental, and vision insurance for you and your dependents
  • 401K plan with company contribution
  • Generous PTO and Parental Leave policies


Interview Accommodations

SQUIRE is committed to working with and providing reasonable assistance to individuals with physical and mental disabilities. If you are an individual with a disability requiring an accommodation to apply for an open position, please email your request to recruiting@getsquire.com and someone on our team will respond to your request.


EEO Provision

SQUIRE provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.


This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.


Pay Transparency Nondiscrimination Provision

SQUIRE will not discharge or in any other manner discriminate against employees or applicants because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant. However, employees who have access to the compensation information of other employees or applicants as a part of their essential job functions cannot disclose the pay of other employees or applicants to individuals who do not otherwise have access to compensation information, unless the disclosure is (a) in response to a formal complaint or charge, (b) in furtherance of an investigation, proceeding, hearing, or action, including an investigation conducted by the employer, or (c) consistent with the contractor’s legal duty to furnish information.


E-Verify Participation

SQUIRE participates in E-Verify. Learn more about E-verify here.

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Average salary estimate

$85000 / YEARLY (est.)
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$80000K
$90000K

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What You Should Know About Sales Trainer, SQUIRE

At SQUIRE, we’re looking for an enthusiastic and skilled Sales Trainer to join our dynamic team in Austin, TX. As a Sales Trainer, you’ll play a vital role in providing top-notch onboarding and ongoing training for our dedicated sales team. This is an exciting opportunity for you to leverage your passion for teaching and helping others succeed in their sales careers. Your job will be to craft engaging training programs that cater to a variety of skill levels, ensuring that each member of our team feels supported and empowered to reach their goals. You’ll work closely with our GTM Enablement team and Sales Leadership to identify areas for improvement, develop robust coaching programs, and fine-tune our existing training materials. Whether you’re facilitating live training sessions or creating interactive eLearning modules, your creativity and expertise will shine through as you transform our sales processes. You’ll have the chance to closely monitor sales performance, offering real-time coaching that turns good sales reps into great ones! SQUIRE values individuals who work collaboratively and possess problem-solving skills, so if that sounds like you, consider joining us on this thrilling journey of growth. Let’s help barbers and shop owners everywhere unlock their fullest potential together!

Frequently Asked Questions (FAQs) for Sales Trainer Role at SQUIRE
What responsibilities does a Sales Trainer at SQUIRE have?

The Sales Trainer at SQUIRE is responsible for developing and implementing training programs aimed at enhancing the skills of our Sales team. This includes revising onboarding processes for new hires, conducting regular call reviews, tracking sales performance, and creating various training materials such as eLearning modules and coaching guides. Overall, the role focuses on fostering a culture of continuous improvement and maximizing sales performance.

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What qualifications are required for the Sales Trainer position at SQUIRE?

To be considered for the Sales Trainer position at SQUIRE, candidates should have at least 1 year of experience in Sales Enablement or Training roles working directly with quota-carrying teams. Alternatively, candidates with 2+ years in an Inside Sales or SDR role may also qualify. Familiarity with sales tools like Salesforce and Salesloft is preferred, along with strong communication and multitasking abilities.

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How does the Sales Trainer role support the sales team at SQUIRE?

The Sales Trainer plays a crucial role in supporting the sales team at SQUIRE by identifying skill gaps and tailoring training programs to meet those needs. Through various methods such as ride-alongs and real-time coaching, the Sales Trainer helps sales reps enhance their performance, ensuring each individual can thrive and contribute to overall revenue growth.

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What does the training program look like for new hires at SQUIRE?

New hires at SQUIRE undergo a comprehensive onboarding program designed by the Sales Trainer. This program includes engaging activities, live sessions, and carefully crafted materials that make learning enjoyable and effective. The goal is to equip new sales members with the necessary tools and knowledge to succeed in their roles from day one.

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What skills will a Sales Trainer develop at SQUIRE?

As a Sales Trainer at SQUIRE, you’ll develop a diverse skill set, including but not limited to effective communication, instructional design, performance analysis, and coaching techniques. You’ll also gain valuable insights into sales methodologies and strategies that can drive business results, enhancing both your personal and professional growth.

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Common Interview Questions for Sales Trainer
Can you describe your experience in training sales teams?

When discussing your experience, focus on specific training programs you developed or facilitated. Include details about the methodologies you used, any successes you achieved, and how you tailored content to meet the needs of different skill levels within the team.

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How do you identify skill gaps in a sales team?

A good approach is to combine sales performance analytics with feedback from sales managers and the team members themselves. Discuss how you’ve previously utilized call reviews or observed interactions to pinpoint areas where training could be implemented for improvement.

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What methods do you use to create engaging training content?

Share your strategies for making training interactive and valuable. This could include incorporating role-playing, using multimedia resources, or blending different learning modalities to accommodate various learning styles, ensuring everyone benefits from the training.

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How do you track the success of your training programs?

Explain how you utilize metrics such as sales performance improvement, participant feedback, and retention of knowledge to measure the effectiveness of your programs. Providing examples of past successes can illustrate your strategies in action.

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Can you give an example of a challenge you faced while training sales representatives?

Discuss a specific instance where you encountered resistance or performance issues. Outline your approach to addressing these challenges, the changes you implemented, and the positive outcomes that resulted from your efforts.

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What is your experience with sales tools like Salesforce or Salesloft?

Highlight your familiarity with sales technologies, describing how you've utilized these tools in training sessions to streamline processes and enhance reps' efficiency, as well as how you have integrated platforms into your training programs.

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How do you stay updated with the latest sales trends and training techniques?

Mention any resources you follow, such as industry publications, professional networks, or online courses that help you stay current in the field of sales training. Communicate your dedication to lifelong learning and professional development.

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Have you had experience creating eLearning materials?

Describe any projects where you developed eLearning courses or modules. Specify the platforms you’ve used and how you ensured the content was interactive, engaging, and effective in conveying essential sales skills.

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What do you believe is the most important quality for a Sales Trainer?

Discuss qualities such as empathy, adaptability, and strong communication skills. Share examples of how these qualities have helped you effectively connect with and motivate sales reps, leading to successful training outcomes.

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How do you provide feedback to underperforming sales reps?

Elaborate on your approach to delivering constructive feedback, emphasizing the importance of being supportive and encouraging. Talk about how you focus on specific behaviors and create actionable plans for improvement, fostering a growth mindset.

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SQUIRE is the world’s leading and fastest-growing software technology company offering a booking and payment platform that connects people with great barbers nationwide.

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BADGES
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BENEFITS & PERKS
Dental Insurance
Disability Insurance
Flexible Spending Account (FSA)
Health Savings Account (HSA)
Vision Insurance
Performance Bonus
Paid Holidays
FUNDING
SENIORITY LEVEL REQUIREMENT
TEAM SIZE
EMPLOYMENT TYPE
Full-time, hybrid
DATE POSTED
March 28, 2025

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