Sasha Ashpis

Engineering Coaching | VP | CTO | ex-Salesforce

I empower individuals and teams to level up their Engineering Leadership skills!

I bring 17+ years of hands-on Silicon Valley technical and leadership experience.

I am passionate about enabling people and teams to avoid unnecessary missteps and grow intellectually.

My goal is for you to produce value as you define it, by learning from my 10,000+ hours of experience.

I live in San Francisco and enjoy playing basketball.

Sasha Ashpis



  • Accrue



    Jun 2021 - Feb 2023

    A Seed stage VC backed startup, focusing on building a SaaS pricing optimization platform for enterprise sales teams to price their quotes using a data-driven approach.

    • Developed the company’s first MVP, which allowed the company to go to market, close initial customers, and raise additional funding
    • Joined as the Head of Engineering and Product and the first full-time employee, before being promoted to CTO in April 2022
    • Created budgets, developed career ladders, hired, onboarded, and led Engineering (7), Product (1), Design (1), and QA (1) teams; including full-time employees and contractors based in the US as well as globally
    • Led teams to self organize through team charters, daily stand ups, and weekly sprints
    • Developed and rolled out cross-departmental systems and processes for the entire organization
  • Lob


    Senior Engineering Manager

    Jan 2020 - Apr 2021

    Lob is a direct mail automation platform

    • Helped lead a YC backed company through a Series B hyper growth phase and Series C funding
    • Grew my organization to a size of 22, where I was the hiring manager for 15
    • Managed 4 managers and built out 5 teams: Core Services, Print and Mail API, Billing, Security, and IT
    • Designed and led the creation of several services that generated $1M+ in ARR upsells
    • Revamped the interview process, pipeline, and training, including coaching in-house tech recruiters
    • Collaborated with leadership to more than double the engineering team to 60+
    • Directed the successful completion of the company’s first SOC II Type 2 audit, with 0 exceptions
  • Augment CXM

    Augment CXM

    Director of Engineering

    Mar 2018 - Jan 2020

    An AI sidekick for customer service agents, with the mission to be agent assist and not agent replace.

    • As Head of Engineering, I hired and led an onsite and remote team of Engineers (8), QA (2), and DevOps (1)
    • Enabled growth from $0 to $1M ARR, by building AI copilot apps for human customer support chat agents
    • Fostered close partnerships with Product, Data Science, Customer Success, and Sales Enablement
    • Formulated and implemented the company’s first Engineering Team Charter and agile processes
    • Spearheaded the transition to containerization (Docker) and orchestration (Kubernetes) for all our microservices (12), which allowed us to scale and set up a dev, staging, demo, and prod environments
  • Salesforce


    Lead Member of Technical Staff

    Jun 2013 - Oct 2017

    Its Salesforce.

    • Joined as part of an acquisition to build and Dreamforce launch the paid Analytics Platform (named Wave at the time)
  • EdgeSpring (Acquired by Salesforce)

    Senior Software Engineer

    Mar 2012 - Jun 2013

    An analytics platform for large data sets with an intuitive UX so technical and non-technical users can do data explorations and analysis. The platform also could create visualizations and ETL pipelines.

    • Led the middleware team to build out v1 of the company CMS system
  • MyVest


    Senior Software Engineer

    Jun 2007 - Mar 2012

    A wealth management platform for RIAs (Registered Investment Advisors) and large institutions.

    • Led 1 of 3 engineers teams and the DevOps team
  • UC Berkeley

    UC Berkeley

    Computer Science graudate

    Jan 2003 - May 2007

    • Earned by Bachelor's Degree in Computer Science

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