Pete Cheslock


Boston, MA

How does this work?

I enjoy improving companies organizational structures, providing insight into building and growing autonomous high functioning, high performing technical teams. I'm fascinated by the dynamics of high performance, and take great pride in building and supporting those teams. I also enjoy the intricacies of Systems Architecture, Design, and Implementation work. I like to use modern tools to solve difficult technology problems. I'm most excited by Automation, Monitoring and Metrics. Some of the non-technical aspects of roles I've had in the past include: * Process improvement and analyzing "how work gets done". * Leveraging "Scrumban" - Mixture between Agile/Scrum and Kanban, useful in technical operations teams with highly interruptive work. * Acting as a technical liaison to the executive team. * Acting as a technical consultant to engineering teams, helping them to design solutions to deploy their applications to production. * Recruiting new engineers to the team * Sharing knowledge with technical communities - All my talks online are available here: I've built and managed teams from 2 to 20. Both local and remote teams. Keeping work flowing using daily standups with skype, google hangous, irc, hipchat, slack, etc. I work to bridge the gap between Engineering, Operations, Product and Business Owners. Passionate for anything related to Automation, Infrastructure as Code, Monitoring/Observability and scaling distributed applications. If you are curious to learn more about my values and how I work - I urge you to watch some of my talks available online (

Ask me about
Cloud Cost Management
Work experience

Oct 2019 - Present

Unaffiliated, LLC.


Startup Advisor and Consultant I created an LLC to take on exciting projects. In one such project, I was the sole expert witness on AWS technologies for two law firms as part of the AWS vs. Microsoft DoD JEDI contract dispute. I researched thousands of documents to analyze the proposals' strengths and weaknesses and the DoD procurement process. I then worked with the legal teams to craft arguments that became the main components of multiple legal briefs and complaints. (This case is still ongoing in the Court of Federal Claims)


Apr 2020 - Mar 2021

The Duckbill Group

Cloud Economist

Your AWS bill is horrifying to look at. We can help you fix it. I work with clients to understand how they use AWS, dive into the cost implications of their architecture decisions, and provide guidance for improvement—finding millions of dollars in savings for our clients. I helped negotiate nearly one billion dollars of enterprise contracts on behalf of our clients.


Oct 2019 - Dec 2019




Aug 2018 - Sep 2019


VP Products

Helping companies store and query more data, spend less money, and run fewer servers. Brought on as one of the founding executives. Helped to define the go-to-market strategy, and refine product direction for launch. Helped to raise the first round of funding, working with the VC's and other executives on due diligence. Worked with team on the inital go-to-market strategy, marketing and messaging, and completed a SOC 2 audit. I spend my time talking with customers, helping us merge our product direction by solving their problems. I assist in all parts of the business from Sales, Marketing, and Recruiting as well as product strategy, go-to-market, and security.


Jul 2014 - Aug 2018

Threat Stack, Inc

VP Technical Operations

Brought on as part of the pre-launch team, I was one of the people involved in the initial architectural design decisions that helped Threat Stack meet our initial launch scale, as well as the continued improvement of the overall platform. Built out and extended much of the original tooling and operational software that we leveraged to manage and maintain uptime requirements of the platform. I have built out the Threat Stack technical operations team with a focus on "Self Service Operations" - essentially working to build software and tools that enable our engineering teams to get access to the resources they need to do their job. We built and manage the systems and tools that allow developers to deploy their code, scale their application, monitor their code, and get alerted when their code is functioning poorly. Some of the technologies we have used to accomplish these goals are: Cassandra (My CTO and I wrote a blog post about our experience Elasticsearch Rabbitmq Kafka Haproxy Graphite Chef Many AWS based services, such as EC2, RDS, ELB, Cloudformation, etc I have acted as the key person managing our operational spend, ensuring that we are able to meet our scale requirements while also meeting key financial targets. Additionally I have worked as a technical architect, helping our engineering team understand tradeoffs when investigating new technologies to solve challenges.

Jan 2013 - May 2014


Director of DevTools

While at Dyn I have been working as a change agent, helping to bring Chef, System Automation, Release Engineering to the engineering and operations teams. We have deployed Chef to hundreds of systems over 20 sites. (FreeBSD & Debian/Ubuntu) Additionally we have released a continuous integration platform with Jenkins & Berkshelf, and Github Enterprise. Providing proper gates for the engineers to ship chef cookbooks. We currently receive chef cookbooks and manage testing/deployment of them from around 50 developers, and expect to see that number double in the next couple months. After we built the CI pipeline around the automation, every new project shipped to production including Chef Cookbooks for deployment (and tests!). Additionally I worked with Chef™ to release and opensource the Omnibus installer for FreeBSD 9.x (which was not previously available). The last project I was involved with was our data-center upgrade project. After seeing the need to modernize our ability to deploy to new bare metal systems, I wrote the initial 20 page spec which detailed out the history, requirements and implementation details. I solicited feedback across various teams and worked with our executive leadership to approve the project. Working with our Head of Data Center & Network Operations, I managed the 3 person team that developed an application to manage every aspect of the systems from power-on, to application deploy. Over the next few months we designed and built a simple asset database, that included IMPI support, remote power control, and integration into our Chef workflow. Even considering the changing technical requirements, and interruptions for production support needs, we were still able to ship this project on time. In the past a new system deploy could be measured in days for OS install, configuration and application deploy. Now we are able to do the same thing within 30 minutes.


Oct 2009 - Jan 2013


Director of Technical and Cloud Operations

While at Sonian (8th employee - 70ish employees when I left) I was involved in everything from pre-sales, support and operations. When I took over the Cloud Operations team we were 3 people (including myself), I helped double the team, introduced a well functioning Scrumban operations workflow and ensured quick delivery of our company requirements. As an early user of AWS - we were one of the top 3 users of S3 and top 5 users of EBS. As an early adopter of cloud services we didn't have good ways of monitoring ephemeral systems, so we created our own way to monitor dynamic workloads and open sourced it - When I took over the team we had ~800 instances on a single cloud (AWS) - our monthly spend was around $450,000. Working with my VP of Eng and Head of Support over 3 months we reduced to ~400 instances and a monthly spend of $200k. I was able to maintain our spend at $200k per month (+/- $10k) while increasing amount of data under management by 200%. When I left Sonian we were managing around 350 Elasticsearch instances across multiple clusters managing around 500TB of data. Additionally I helped Project Manage the successful deployment of our application to the IBM SmartCloud one month ahead of schedule. Over the next 6 months we deployed our application to both the Rackspace Cloud and HP Cloud. The deploy of our application to all 3 clouds included hands-on Chef work as well and project management.

Dec 2006 - Oct 2009

McGladrey (Formerly Caturano and Company)

Senior Technology Consultant

• Work to present and implement technology solutions to business from 100-10,000 employees • Design and implement server consolidation solutions utilizing VMware ESX server and VMware Capacity Planner. • Organize customer requirements for technology solutions, present them with a cost effective strategy to meeting their company’s technology goals • Meet with current and prospective clients to review technology strategy and goals. • Help clients prioritize and budget their technology expenditures, training them on new technologies such as server and storage virtualization, that can enable them to reduce costs and save money in the long term. • Help find new business by reviewing the current state of a companies technology infrastructure, and making recommendations on how to better secure, manage, or operate their environment.


Oct 2006 - Dec 2006

Collax Inc.

Pre-Sales and Support Engineer

• Was part of a 3 person team to launch a new Linux based small business server to the US market. • Created clearly defined procedures around how we sell support contracts, including defining tiers and SLA’s to our growing customer base. • Helped to create and define training modules that our customers and reselling partners would use to train their staff. Creating a “Collax Server” certification program based on our product suite. • Supported the sales teams in the US and Germany to respond to RFI/RFP, as well as giving in-depth technical training and overviews to new and potential partners. • The company was unable to attain funding to sustain the US launch and the office was shut down shortly after creation.

Aug 2004 - Jul 2006


Pre-Sales and Systems Engineer

• Acted as the technical consultant on our sales team, giving in depth technical overview presentations of our product line to a range of technical and non-technical people. • Created and edited presentations to ensure that they reflected the current and future abilities of our products. • Created and managed various demo/Proof of Concept installations of our products for testing and sales demonstration purposes. • Presented software training sessions to increase the knowledge level of support and sales teams. • Designed, installed and implemented highly-available advanced messaging management software architecture for our clients. • Head of external facing field testing (beta test) for next-generation messaging management software. • Lead engineer for the installation, configuration and support of several multi-node, enterprise class software architectures. • Experience with Relational DB’s(SQL), Apache, load balancing and highly available Linux software technologies.

Jan 2002 - May 2004


Network Engineer

- Designed and Setup a cost effective solution to remove numerous SPAM and virus emails from our mail servers before they reached the corporate network - Design, implement, install and troubleshoot multiple LAN/MAN/WAN networks ranging from wireless, ethernet and fiber. - 2nd and 3rd Level supports for our Linux and Windows servers, including complete server rebuilds and restore. - 1st and 2nd level LAN and WAN support, as well as OS support to over 300 clients with numerous end users. - Designed and setup a disaster recovery program to create an automated failsafe/fail proof recovery of our largest trafficked servers. - Designed, built and maintained servers with Windows 2000 server, 2003 server, and Linux - In depth knowledge of Sun Cobalt Linux servers including Raq3, Raq4 and RaqXTR


2009 - 2012

Babson College - Franklin W. Olin Graduate School of Business

Masters in Business Administration

2000 - 2004

Michigan State University

BA, Communications

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