Back to jobs

Technical Trainer

About Files.com

Files.com is an enterprise secure file transfer & automation app with over 4,000 paying business customers, including Target, Canonical, UPS, Leica, DirecTV, GoPro, Marriott, and more.

Files.com was bootstrapped by our founder and has been profitable since its founding in 2010. We recently raised $46.5 million of growth equity from Silicon Valley-based Riverwood Capital to accelerate our growth.

Location: Work From Your Home on a Remote-First Team at a Hybrid Remote Company

World Class Pay and Benefits

In-House Training: You have the technical skillset of an Implementation Engineer, Success Engineer/Architect, Sales Engineer or Senior Tech Support Engineer already. You are familiar with coordinating customer engagements to implement and configure SaaS technical solutions. We will take your finely honed technical skills and provide you with a combination of different training methods that will bring you up to speed on our processes, tools, and tech.

Big Company Benefits: You'll get full 🏥 Health/Dental/Vision Insurance coverage (plus 75% of Spouse/Family coverage too), 💰 401(k) with generous matching, 🎄 11 Company Holidays per year, and 🏖 20 PTO/Vacation days, plus we give employees off for Winter Break at the end of the year!

Company Macbook Pro and $1,000: We'll send you a company issued contemporary Macbook Pro as well as $1,000 sign-on bonus as a welcome to Files.com.

100% Remote Opportunity

The Files.com Customer Success team is 100% remote. However, we travel for regular in-person meetings with the team and the entire company to meet and work together face to face. These meetings are in cities around the US, including Scottsdale, Austin, Orlando, New Orleans, San Diego, Las Vegas, and New York City.

In-person events combine work and fun and are designed to make up for the in-person interaction that occurs in an office job.

As a Technical Trainer, your role is to design and deliver large-scale training sessions focused on integrations, automations, and the technical capabilities of Files.com. You will be responsible for building training programs, developing webinars, white papers, and creating supplemental materials for both new and existing customers.

Unlike traditional customer success roles, this position is focused on one-to-many training delivery rather than one-on-one interactions. Your goal is to empower our customers by equipping them with the knowledge and skills they need to fully utilize Files.com’s platform and features. You will work closely with internal teams to identify key topics and create training materials that support our customers’ technical needs and growth.

In this role, you will:

  • Develop Training Programs: Identify key training topics related to integrations, automations, and Files.com’s platform. Build scalable training materials including webinars, white papers, best practices documentation, and videos.
  • Deliver Large-Scale Training: Lead webinars, virtual workshops, and large-scale training events for diverse customer groups.
  • Create Educational Materials: Build supplementary materials such as technical guides, FAQs, and training decks for use in webinars and for sales collateral. Identify customer pain points and tailor training to address technical challenges based on feedback from customer success, support, and sales teams.
  • Stay Up-to-Date on the Platform: Continuously update training content to reflect the latest product features, enhancements, and best practices.
  • Measure Success: Use feedback and engagement metrics to measure the effectiveness of training programs and identify areas for improvement.
  • Standardize Training Processes: Help build repeatable processes and templates to streamline the creation and delivery of training materials.
About You:

  • Technical Background: You have a strong foundation in SaaS infrastructure, integrations, or technical systems. You’ve worked in roles such as Implementation Engineer, Sales Engineer, or Senior Tech Support Engineer.
  • Training Experience: You are passionate about teaching and can explain complex technical topics to diverse audiences. Experience in delivering large-scale technical training is highly valued.
  • Webinar and Content Creation: You’re comfortable hosting webinars, creating technical white papers, and developing supplemental materials like guides, FAQs, and documentation.
  • Proactive & Detail-Oriented: You excel at identifying areas where training will have the most impact and proactively create programs that address those needs.
  • Strong Communication Skills: You have excellent verbal and written communication skills and can break down complex topics into simple, understandable terms.
  • SaaS Expertise: You have a general understanding of SaaS environments and are familiar with technologies like APIs, internet communication protocols, file integration tools (AWS, SharePoint), and identity management platforms (Okta, Azure AD).

Apply for this job

*

indicates a required field

Resume/CV*

Accepted file types: pdf, doc, docx, txt, rtf


We would like you to tell us why this opportunity speaks to you. You don’t have to tell us now, but we promise we’ll read your story upfront. You’re more than a resume!

Select...
Select...
Select...
Select...
Select...
Select...
Select...

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in Files.com’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Select...
Select...
Race & Ethnicity Definitions

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

Select...

Voluntary Self-Identification of Disability

Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 04/30/2026

Why are you being asked to complete this form?

We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.

Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.

How do you know if you have a disability?

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:

  • Alcohol or other substance use disorder (not currently using drugs illegally)
  • Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
  • Blind or low vision
  • Cancer (past or present)
  • Cardiovascular or heart disease
  • Celiac disease
  • Cerebral palsy
  • Deaf or serious difficulty hearing
  • Diabetes
  • Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
  • Epilepsy or other seizure disorder
  • Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
  • Intellectual or developmental disability
  • Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
  • Missing limbs or partially missing limbs
  • Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
  • Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
  • Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
  • Partial or complete paralysis (any cause)
  • Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
  • Short stature (dwarfism)
  • Traumatic brain injury
Select...

PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.