SaaS Sales Lead Instructor (U.S. based - Remote/Consultant)

ABOUT GENERATION
At Generation, we believe in the power of employment to change lives. We are a global nonprofit organization that supports adults to achieve economic mobility through employment. Generation trains and places adult learners of all ages into careers that are otherwise inaccessible, working in partnership with governments, employers, and other system actors. We also conduct original research and share data insights on high priority global workforce transition topics to inform decision-making by workforce system stakeholders. Launched in 2015, Generation comprises a global hub (Generation You Employed, or GYE) and a network of in-country affiliates. To date, the network has 100,000+ graduates and 11,000+ employers across 46 professions and 17 countries.
When learners join Generation, +1% are unemployed, of which nearly half are long-term unemployed. Three months after completing our program, graduates have a 78% job placement rate, rising to 88% within six months. Of our employed graduates, 68% are hired by repeat employers who have previously hired Generation graduates, and 8+% are in jobs directly related to the profession for which we have trained them. Employed graduates immediately earn an average of 3-4X their previous earnings. Two to five years after graduation, 77% of our alumni from upper-middle income countries continue to meet their daily financial needs and 63% can save for the future. To date, Generation’s global graduates have earned more than $1 billion in wages. Generation graduates typically have a secondary school background, 54% are female, 34% have dependents, and the majority identify with underrepresented communities in their country.
ABOUT THE ROLE
We are seeking a dynamic and experienced Instructor to support the training for the Sales Development Representative (SDR) role in the Software as a Service (SaaS) sector who is motivated by Generation’s mission and driven by the objective of helping learners begin a new career. You will play a pivotal role as we establish our US operations through fully remote program delivery and job placements. We plan to use this program to create data insights on conditions for successful remote work so we may expand beyond West Virginia to serve all rural US communities. Your efforts will contribute to changing the lives of unemployed and underemployed individuals seeking economic stability and mobility.
For the pilot phase, we are looking for a full-time contractor for specific periods of time, as follows:
Job Type: Full-Time Contractor (40 hours per week)
Start Date: April 16 , 2025
Job Duration: April 16 - Nov 28 to support 2 cohorts
Location Requirements: Remote (with access to strong WiFi), based in the U.S. and able to work from 8 am - 5 pm EST (with an hour unpaid lunch break)
Please note that the start date and job duration are subject to change based on final program design and launch timelines. This will be confirmed by the time of hiring.
RESPONSIBILITIES
1. "SaaS Sales” Online Training Facilitation (80%):
Provide quality, effective, rigorous, relevant and adapted training to an adult audience
Become familiar with and follow the course of the program as designed by Generation
Manage the involvement and active participation of our learners in the training program
Establish a strong culture of learning and teaching and ensure a positive and inclusive learning environment
Build strong and trusting relationships with learners, develop a detailed knowledge of their strengths and challenges while ensuring a caring learning environment, and conduct office hours and/or provide other strategic learning opportunities to support learners
Oversee learner progress by frequently reviewing and analyzing learner data (e.g., reviews attendance, assignments, assessments, etc.), grading assignments and assessments, leveraging relevant digital tools like Salesforce, and suggest and implement strategies to support learner needs (e.g., offer office hours, add refresher content, etc.)
Take into account the feedback and results of learners and adapt teaching accordingly
Monitor and respond to learners' messages and requests on our communication channels (e.g. Teams, Slack)
Conduct assessments and ensure data is accurately recorded by the assistant instructor, and learner progress is regularly reported and reviewed in Canvas, Salesforce, and other relevant platforms.
Share feedback with the Generation team and implement the recommendations to guarantee quality training for our learners
Effectively use digital tools such as Teams, Canvas, Slack, and GDrive to perform daily instructional tasks

2. Supplementary Activities (20%):
Actively collaborate with the Generation team to identify and effectively counter obstacles to learners' success and transition into a professional environment
Participate in the organization of the cohort launch (e.g., lead pre-program orientation sessions, collaborate with delivery team and mentors, etc.)
Advising and supporting micro-internship design as needed
Attend onboarding sessions as agreed with the management team before cohort launch
Take part of coaching cycles determined per management with specified cadence; this could include instructional team meetings, coaching conversations, participating in communities of practice and/or take part of specific professional development activities for upskilling such as attending workshops/trainings
Lead and coordinate with delivery team, particularly the assistant instructor
Coach and develop the Assistant Instructor
INSTRUCTOR CRITERIA
Experience and Technical Skills:
A bachelor’s degree in any field or equivalent work experience
A minimum of 3 years of relevant – hands-on – professional experience in B2B Sales. This could be as an SDR/BDR and/or managing SDRs/BDRs, preferably at a SaaS company. Professional experience may include:
o Conducting lead generation and lead qualification for outbound and inbound contexts is a must. Experience with the remaining parts of the sales cycle (demonstration, negotiation, and closing) is a plus but not required.
o Having in-depth knowledge and hands-on experience with CRM systems (HubSpot preferred, Salesforce also accepted) and its functionalities, including automation, analysis, and customization
o Analyzing and leveraging sales metrics to drive performance improvements using the above-mentioned CRM systems
o Mentoring and coaching sales professionals to enhance their skills and achieve their targets
o Leveraging sales enablement tools such as Outreach, SalesLoft, or Gong.
At least 1 year of proven experience facilitating on-the-job SDR/BDR Training/Coaching. Experience as a professional adult trainer is essential.
2+ years of HubSpot experience and confidence in teaching key HubSpot sales tools used in the program without detailed instructor guides. (Strongly preferred)z
Passion for helping change the life trajectories of unemployed and/or at-risk youth.
Professional certifications from Hubspot or motivation to obtain necessary Hubspot certifications on the job is a must
At least 1 year of experience managing small teams (e.g., team building, collaboration, professional growth and development, coaching) is preferred
Being up-to-date with the latest trends, methodologies, and opportunities in Sales. Specific knowledge on SaaS sales is a plus.
Strong command of digital tools is key, in particular: G Suite, Teams, Slack, and Outlook
Proven track record with LMS platforms to manage and deliver training content (Canvas preferred)
Excellent communication skills (writing + oral expression that can work for different audiences)
Mindsets and abilities:
Embody values and understand the future challenges and opportunities for youth empowerment and is passionate about creating an impact in the employment ecosystem
Identify with the mission of Generation
Demonstrate an interest in the intersection of social and educational initiatives and genuine enthusiasm and passion for teaching and facilitation
Demonstrate resilience as well as great adaptability and flexibility
Demonstrate great motivation and empathy to support groups of young adults who are facing barriers to employment
Work rigorously and independently
Thrive in a fast-paced and dynamic work environment
Creative problem-solving abilities to address training challenges and learner needs
Demonstrate proactiveness, personal responsibility and a strong commitment towards self-reflection and growth
Dedication to supporting learners that need additional support and guidance in order to achieve mastery.

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