Edtech.com's Summary

Yourway Learning is hiring a Director, Sales Operations to build and manage systems, training, tools, and cross-functional processes that enable sales teams in the US and LATAM to qualify opportunities, advance deals, and increase win rates in the K–12 market. This role drives sales enablement, proposal development, procurement support, CRM discipline, and collaboration with marketing and client success teams to ensure effective sales execution and operational consistency.

Applicants should submit a cover letter and resume to info@yourwaylearning.com, with the subject line "Director, Sales Operations".

Highlights

Lead sales enablement strategy, including onboarding, training, coaching, and process improvements.
Develop and maintain training programs covering products, sales methodologies, purchasing practices, and competitive positioning.
Manage proposal development, RFP responses, procurement support, and cooperative purchasing documentation.
Ensure CRM adoption, pipeline management, forecasting accuracy, and sales process discipline.
Collaborate cross-functionally with Sales, Marketing, Product, Client Success, and Account Management teams.
Require 4+ years’ experience in sales enablement, operations, or proposal management in complex B2B or public-sector environments.
Strong knowledge of K–12 district procurement, RFP processes, funding sources, and proposal development.
Experience with CRM and sales enablement tools, and ability to drive their adoption and reporting.
Compensation includes $95,000–$105,000 base salary plus quarterly bonuses and benefits such as medical, dental, 401(k), and PTO.
Candidates must be willing to travel up to 25% domestically and occasionally to LATAM; bilingual English-Spanish preferred.

Director, Sales Operations Full Description

The Director, Sales Operations is responsible for building the systems, training, tools, content, and cross functional processes that help the sales organizations (US and LATAM) qualify opportunities effectively, advance deals efficiently, and improve win rates across the K–12 market.

This role serves as the operational backbone of the sales organizations, ensuring that sales representatives have the resources, training, market knowledge, procurement support, proposal materials, and process discipline necessary to execute consistently and at scale.

The Director, Sales Operations partners closely with Sales, Marketing, Product, Client Success, and Account Management to ensure the commercial teams are equipped to support district purchasing processes, navigate complex stakeholder environments, and communicate the value of Yourway’s solutions effectively.

This includes resellers and distributors, as well as government agencies in LATAM. This role owns sales onboarding, sales process adoption, proposal and RFP support, procurement readiness, CRM discipline, sales training, and field enablement across the revenue organizations.

Because Yourway is a growing organization, this leader must be able to operate independently with minimal ramp-up time. The ideal candidate brings significant experience supporting K–12 district sales organizations and can immediately contribute to proposal development, procurement support, sales process execution, and team effectiveness.

Reports To: VP of US Sales
Department: Sales
Location: Remote / Field
FLSA Status: Exempt

Key Responsibilities

Sales Enablement & Team Effectiveness

Lead the design and execution of the sales enablement strategy, including onboarding, training, coaching resources, sales plays, and process improvement initiatives that help the team qualify opportunities, advance deals, improve win rates, and strengthen forecasting accuracy.
Develop and maintain onboarding and ongoing training programs covering Yourway products, sales methodologies, district purchasing practices, funding opportunities, competitive positioning, and sales best practices.
Build and maintain sales resources, including discovery frameworks, qualification criteria, demo expectations, talk tracks, objection-handling guides, stakeholder-specific use cases, and competitive positioning.
Establish and reinforce standards for CRM use, pipeline management, sales-stage progression, forecasting, and adoption of the Yourway Sales Process.
Partner with sales leadership to identify enablement needs and continuously improve seller effectiveness through training, resources, and operational support.

Proposal Development, Procurement & Deal Support

Lead proposal development, RFP responses, procurement support, cooperative purchasing documentation, security reviews, and other pre-sales activities that support revenue generation.
Maintain expertise in K–12 purchasing processes, including district procurement workflows, state contracts, BOCES purchasing mechanisms, cooperative purchasing agreements, and funding sources.
Support sales representatives in aligning opportunities to available funding sources and preparing for stakeholder meetings, demonstrations, working sessions, and proposal presentations.
Coordinate agreement workflows and signature collection to support timely progression from proposal to executed contract.

Sales Operations & Cross-Functional Collaboration

Drive effective use of CRM and sales tools through standards, training, reporting, and operational processes that improve visibility and consistency across the sales organization.
Monitor sales-stage progression and provide reporting, analysis, and recommendations to improve deal movement and overall sales effectiveness.
Collaborate with Marketing, Product, Client Success, and Account Management to improve lead quality, strengthen messaging, support successful customer transitions, and ensure alignment across the customer lifecycle.
Maintain sales documentation, playbooks, templates, process guides, and enablement resources used across the organization.

Qualifications

Required

4+ years of experience in sales enablement, sales operations, proposal management, revenue operations, or a related commercial function supporting complex B2B or public-sector sales environments.
Demonstrated success in building and scaling sales processes, training programs, sales plays, enablement resources, and operational systems that improve seller effectiveness and deal progression.
Experience supporting K–12 school districts, educational, government, or other public-sector sales organizations, including RFP responses, procurement processes, proposal development, and cross-functional deal coordination.
Strong understanding of CRM and sales enablement tools, with a proven ability to drive adoption, process discipline, reporting, and operational consistency.
Excellent written and verbal communication, project management, stakeholder management, and facilitation skills.
Ability to collaborate effectively across Sales, Marketing, Product, Client Success, and Account Management.
Familiarity with federal, state, and local funding sources that influence district purchasing decisions.
Comfortable operating in a fast-paced, growth-oriented environment with evolving priorities.
Willing and able to travel approximately 25% of the time domestically, depending on the season and selling cycle. LATAM travel is scoped for once or twice a year.

Preferred

Experience writing and supporting successful responses to district, state, and cooperative purchasing RFPs.
Experience supporting K–12 purchasing processes, including RFPs, cooperative purchasing agreements, state contracts, BOCES purchasing mechanisms, and district procurement workflows.
Experience working with and supporting resellers and distributors.
Experience supporting educational technology, curriculum, professional learning, instructional services, or related K–12 solutions.
Understanding of district budgeting cycles, cabinet-level decision-making, instructional priorities, and educational purchasing processes.
Bilingual in English and Spanish — speaking, reading, and writing.

Core Competencies

Sales Operations & Process Management
K–12 Procurement, Funding & RFP Expertise
Sales Enablement & Training
Project & Stakeholder Management
Communication & Influence
Cross-Functional Collaboration
Relationship Building
Continuous Improvement

Measures of Success

High adoption of the Yourway Sales Process, CRM standards, and enablement resources.
Timely and accurate completion of proposals, RFPs, procurement documentation, and contracting support.
Increased sales team effectiveness in discovery, solution validation, proposal development, and deal progression.
Forecasting accuracy.
Consistent sales process execution and pipeline visibility across the organization.
Strong cross-functional alignment that supports revenue growth and customer success.

What We Offer

Compensation: $95,000–$105,000 annual base salary plus bonus, paid quarterly.
Yourway offers medical, dental, vision, and other insurance benefits, a 401(k) retirement plan, transit benefits, medical spending, and dependent care benefits.
$100/month phone reimbursement.
Up to 15 days PTO, along with additional company holidays.
Collaborative, supportive team culture.
Mission-driven work that makes a real impact in K–12 education.

Don’t check off every box in the requirements listed above? Please apply anyway! Studies have shown that marginalized communities — such as women, LGBTQ+ people, and people of color — are less likely to apply to jobs unless they meet every single qualification. Yourway Learning is dedicated to building an inclusive, diverse, equitable, and accessible workplace that fosters a sense of belonging. So if you’re excited about this role but your past experience doesn’t align perfectly with every qualification in the job description, we encourage you to still consider submitting an application. You may be just the right candidate for this role or another one of our openings.

Yourway Learning is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

Original Job Description

Sales Enablement & Team Effectiveness

Lead the design and execution of the sales enablement strategy, including onboarding, training, coaching resources, sales plays, and process improvement initiatives that help the team qualify opportunities, advance deals, improve win rates, and strengthen forecasting accuracy.
Develop and maintain onboarding and ongoing training programs covering Yourway products, sales methodologies, district purchasing practices, funding opportunities, competitive positioning, and sales best practices.
Build and maintain sales resources, including discovery frameworks, qualification criteria, demo expectations, talk tracks, objection-handling guides, stakeholder-specific use cases, and competitive positioning.
Establish and reinforce standards for CRM use, pipeline management, sales-stage progression, forecasting, and adoption of the Yourway Sales Process.
Partner with sales leadership to identify enablement needs and continuously improve seller effectiveness through training, resources, and operational support.

Proposal Development, Procurement & Deal Support

Lead proposal development, RFP responses, procurement support, cooperative purchasing documentation, security reviews, and other pre-sales activities that support revenue generation.
Maintain expertise in K–12 purchasing processes, including district procurement workflows, state contracts, BOCES purchasing mechanisms, cooperative purchasing agreements, and funding sources.
Support sales representatives in aligning opportunities to available funding sources and preparing for stakeholder meetings, demonstrations, working sessions, and proposal presentations.
Coordinate agreement workflows and signature collection to support timely progression from proposal to executed contract.

Sales Operations & Cross-Functional Collaboration

Drive effective use of CRM and sales tools through standards, training, reporting, and operational processes that improve visibility and consistency across the sales organization.
Monitor sales-stage progression and provide reporting, analysis, and recommendations to improve deal movement and overall sales effectiveness.
Collaborate with Marketing, Product, Client Success, and Account Management to improve lead quality, strengthen messaging, support successful customer transitions, and ensure alignment across the customer lifecycle.
Maintain sales documentation, playbooks, templates, process guides, and enablement resources used across the organization.

Qualifications

Required

4+ years of experience in sales enablement, sales operations, proposal management, revenue operations, or a related commercial function supporting complex B2B or public-sector sales environments.
Demonstrated success in building and scaling sales processes, training programs, sales plays, enablement resources, and operational systems that improve seller effectiveness and deal progression.
Experience supporting K–12 school districts, educational, government, or other public-sector sales organizations, including RFP responses, procurement processes, proposal development, and cross-functional deal coordination.
Strong understanding of CRM and sales enablement tools, with a proven ability to drive adoption, process discipline, reporting, and operational consistency.
Excellent written and verbal communication, project management, stakeholder management, and facilitation skills.
Ability to collaborate effectively across Sales, Marketing, Product, Client Success, and Account Management.
Familiarity with federal, state, and local funding sources that influence district purchasing decisions.
Comfortable operating in a fast-paced, growth-oriented environment with evolving priorities.
Willing and able to travel approximately 25% of the time domestically, depending on the season and selling cycle. LATAM travel is scoped for once or twice a year.

Preferred

Experience writing and supporting successful responses to district, state, and cooperative purchasing RFPs.
Experience supporting K–12 purchasing processes, including RFPs, cooperative purchasing agreements, state contracts, BOCES purchasing mechanisms, and district procurement workflows.
Experience working with and supporting resellers and distributors.
Experience supporting educational technology, curriculum, professional learning, instructional services, or related K–12 solutions.
Understanding of district budgeting cycles, cabinet-level decision-making, instructional priorities, and educational purchasing processes.
Bilingual in English and Spanish — speaking, reading, and writing.

Core Competencies

Sales Operations & Process Management
K–12 Procurement, Funding & RFP Expertise
Sales Enablement & Training
Project & Stakeholder Management
Communication & Influence
Cross-Functional Collaboration
Relationship Building
Continuous Improvement

Measures of Success

High adoption of the Yourway Sales Process, CRM standards, and enablement resources.
Timely and accurate completion of proposals, RFPs, procurement documentation, and contracting support.
Increased sales team effectiveness in discovery, solution validation, proposal development, and deal progression.
Forecasting accuracy.
Consistent sales process execution and pipeline visibility across the organization.
Strong cross-functional alignment that supports revenue growth and customer success.

What We Offer

Compensation: $95,000–$105,000 annual base salary plus bonus, paid quarterly.
Yourway offers medical, dental, vision, and other insurance benefits, a 401(k) retirement plan, transit benefits, medical spending, and dependent care benefits.
$100/month phone reimbursement.
Up to 15 days PTO, along with additional company holidays.
Collaborative, supportive team culture.
Mission-driven work that makes a real impact in K–12 education.

Yourway Learning is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

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