TrustYou (previously CheckMate)

CheckMate’s mission is to connect businesses and their customers through real-time, human communications.

Founded 2013
16-50 employees
  • Enterprise Software
  • Headquarters address
    1061 Market St #200, San Francisco, CA 94103, USA

    The CheckMate Story

    In early 2013, Drew, Brian and Anthony set out to transform the customer experience for hotel guests under the premise that every customer should be able to easily communicate with their hotel. They assembled in San Francisco and started building a talented team to tackle this massive challenge.

    Later that year, CheckMate joined forces with Room 77, a best-in-class technology company. Their management team and investors have deep experience with travel and entrepreneurship, having built companies like, Farecast, Zillow and Jetsetter. The business is well capitalized from investors including Sutter Hill, General Catalyst, Altimeter and strategic investors Concur and Expedia.

    Since then, we've expanded our vision to enable all types of service businesses to engage in seamless, modern communications with their customers. We work with hotels, serviced apartments, ski resorts, golf courses and other "service businesses" to create transformative consumer experiences.

    We pay well, strike a balance between work and play, and have fun together while building a world-class business.

    How We Interview & Hire

    Our goal is to hire the brightest, most passionate and hard working individuals we come across -- in all areas of the organization.

    We start our interview process with an hour long phone call to discuss the position and the company. Following a call, we invite candidates into our office to meet the entire team and conduct pair-programming exercises. Candidates that exceed expectations will receive a formal offer shortly after their visit.

    Our Culture & Perks

    With origins in the hospitality industry, we take travel seriously. All employees receive an annual travel stipend (and generous vacation policy) to encourage visiting new destinations. When we're not traveling, our office in San Francisco's is lively and buzzing. We bring in daily lunches and celebrate our successes at frequent happy hours.

    We have a casual atmosphere, but we are performance-oriented, focused and competitive around our business. We value hunger, drive and initiative. We are collaborative, respectful of each other and of our customers. And we strive to build best-in-class product.

    Tech stack

    Rails, EmberJS, Postgres, HAML, SASS, Redis, Memcached, Heroku, AWS (EC2/RDS/ELB/S3)


    Compensation and retirement

    401k plan

    Health and wellness

    Insurance (Health)
    Insurance (Dental)
    Insurance (Vision)
    Insurance (Life)
    Insurance (Disability)

    Values and quality of life

    Catered meals
    TrustYou (previously CheckMate) - We eat, drink and brainstorm in "the booth."
    TrustYou (previously CheckMate) - We hold team off-site meetings to discuss our goals and values
    TrustYou (previously CheckMate) - When we run out of whiteboards, we take to the walls
    TrustYou (previously CheckMate) - During "off hours" you might find us at a Cal game or competing in our kickball league
    TrustYou (previously CheckMate) - We take coffee breaks seriously, and serious coffee breaks
    TrustYou (previously CheckMate) - We will publicly shame you for using a selfie stick
    TrustYou (previously CheckMate) - Does anyone remember that Napa trip? Didn't think so.
    TrustYou (previously CheckMate) - We're a close team & we get weird together