Head of Training

  • StreetLight Data
  • San Francisco, CA
  • May 15, 2021

Job Description

StreetLight Data, the pioneer in Big Data for mobility, is revolutionizing transportation and urban planning to help the world better deploy infrastructure and adapt to new forms of mobility. From legacy systems to ride sharing and bike sharing to autonomous vehicles, our platform powers 6,000+ mobility projects every month for government and private clients, and we're just getting started.
A newly created position at StreetLight Data reporting initially to the Chief Operating Officer, the Head of Training will be responsible for developing and improving the training organization’s business plan, service offerings, processes, execution, deliverables and personnel in a manner that delivers high levels of customer satisfaction to both internal and external constituencies, creates strong internal operational efficiencies and positions the organization to operate at a break-even level within 3 years.
Location: We are flexible on the location of this position - it could be in any one of our three offices (San Francisco, CA, Richmond, VA, or Vancouver, BC) - or remote with the US or Canada.

Key Responsibilities:

  • Business Leadership:
As a business leader driving outcomes aligned to corporate goals, you will:
  • Develop with consultation from sales, marketing, finance and senior leadership, a business plan your department supports the achievement of corporate goals and deliver high levels of customer satisfaction, revenue retention and expansion, including:
  • Developing, testing, launching and managing training offerings
  • Developing, testing, launching and managing pricing plans where applicable
  • Supporting revenue targets, where applicable
  • Setting operational goals for the training team that supports meeting corporate objectives for revenue retention and expansion, customer satisfaction and operational efficiencies 
  • Managing employees daily performance and collaborating with your leadership to establish salary and bonus structures that support operational and financial goals
  • Measuring and managing your organization’s KPIs and progress towards attainment of operational and financial goals
  • Creating and maintaining systems of continuous improvement across your teams and in collaboration with other StreetLight teams that:
  • Leverages the collective skills, knowledge and experience of team members
  • Rapidly assimilates learnings to develop best practices
  • Produces high quality work products aligned with corporate messaging
  • Ensures maximal operational efficiencies and customer satisfaction

  • Training Leadership:
As the leader of the organization that delivers training for customer, partner and employee constituencies, you will grow and manage a team of 2-3 initially and collaborate with them to collectively achieve the following:
  • Maintain and improve our curriculum and curriculum development methodology, processes and standards using an efficient, leveraged approach to internal knowledge capture and core content development (e.g. including internal and customer-facing Documentation, Sales and Technical Sales Enablement assets, etc.); ensuring Training content is kept current with monthly product releases across changes in UI/UX, features and functionality;  developing and delivering engaging, accessible and effective end-user course design and content assets across learning channels (online courses and certifications, in-person ILT, online ILT) and constituencies
  • Establish a strong, results-oriented culture by leading from the front and personally participating in the research of employee and customer training needs, development of curriculum, ILT courseware and eLearning courseware, and delivery of training to StreetLight Data employees and customers
  • Research, develop, test, launch, manage, maintain and improve a training roadmap for each constituency including working closely with COO and your training team to:
  • Understand the capabilities and limitations of MindTickle, our employee training online / ILT curriculum management and delivery platform
  • Understand the capabilities and limitations of Skilljar, our customer training online / ILT curriculum management and delivery platform
  • Understand the capabilities and limitations of Articulate Rise, our customer course development toolResearching and defining attributes and needs of user personas for each constituency
  • Understanding internal training personas as StreetLight scalesResearching certification / professional education requirements for different customer job titles and completing the process wherever possible to enable StreetLight education to “count” for these requirements
  • Identifying revenue opportunities across customer and partner constituencies 
  • Understanding training needs of user personas and developing a roadmap of training offerings for each constituency, including employee basic and advanced training, and a mix of basic (included for all customers) and premium or a la carte (additional cost) offerings

Skills & Qualifications:

  • Bachelor's degree required, preferably in a technical field such as civil engineering, transportation planning, information technology or related. MBA a strong plus
  • Minimum of  2-3 years running a training organization
  • Direct, personal experience providing instructor led training programs to enterprise level customers a strong plus
  • Ability and willingness to develop product expertise for StreetLight Data’s mobility platform, applications and new products as they come online. This position is expected to lead from the front with their grasp of product knowledge and commitment to continuous learning. 
  • Proven ability to provide curriculum strategies in a technical field for delivery through multiple channels (online, ILT, etc) and serving multiple audiences 
  • Experience in developing and delivering online courseware to onboard new customers and provide support for expert and enhanced product usage through ILT and online channels
  • Experience developing and delivering certification programs for a technical field a strong plus
  • Proven ability to hire, onboard, manage and ensure ongoing skills and knowledge development across support and/or training organizations of 5 people or more
  • Management experience dealing with a range of employees from new college graduates to seasoned professionals, understanding of how to build successful team-based organizations that are aligned to corporate goals and operate with high efficiency and morale
  • Skilled at working closely with product and sales organizations to satisfy the needs of sales constituents (sales management, sales reps, customer success and solutions engineering) requirements for support and training of customer organizations and individuals, and training of internal constituents. Past experience collaborating with and supporting Account Management / Customer Success organizations with customer retention goals a strong plus
  • Comfortable operating in a fast paced, multitasking environment that requires rapid context switches for successful execution
  • Strong presentation and communication skills in all forms, written, verbal, in person and video formats
StreetLight Data is an equal opportunity/affirmative action employer. StreetLight Data 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.

Organization Type


Organization Size



Buildings & Cities

Drawdown solutions

Bicycle Infrastructure, Electric Bikes, Electric Cars, Public Transit, Walkable Cities

Want us to tweet your job? Please write your organization's twitter username below (just the username, please do not add the '@')