SendGrid’s history with Agile

I thought I’d highlight the milestones SendGrid has had in our Agile journey.

Ground Zero

When I started at SendGrid in May 2011, the organization was on the verge of adopting Agile and Rally’s agile software solution. In other words, the decision to move to Agile had been made prior to my start. (In fact, it was a key selling point used to get me to join SG.) The company was barely 18 months old, still a start up and had an Engineering staff of 10-15, tops.

Hired as the first project manager and Agile coach, I was responsible for putting the training strategy together. We had inroads with Rally b/c Chad (our CFO) had also been employee #7 at there, and they were in Boulder (as are we).

Prior to using Rally’s tool, SG had been using Redmine to store all features and defects. There were no formal teams either.

Agile training, Rally style

Within my first couple weeks, I met with Ann Konkler (Rally certified trainer) and we drafted a schedule for the following visits:

  1. phone conversation to set stage
  2. visit to Boulder to meet with stakeholders (I was present, though our VP of Eng still had not started)
  3. two-days of training in Anaheim with all Engineering staff (VP Eng now present)
    • for the first iteration, we converted all US to physical note cards (sticky notes) and placed them on the walls, per team
    • no use of tool at this time
  4. after 2 weeks (iteration length), a follow-up with Ann in Anaheim with Engineering staff
  5. after additional 2 weeks, hosted addt’l Rally trainer for two-day training on Rally SW

Ann also followed up via email/phone. When the whole organization (young and small as we were) is making the transition to Agile, having a trainer on-site and dedicated for those first weeks is critical.

We adopted Rally’s tool for managing our projects, and I created some custom panels (views / queries) using javascript. It provides a very powerful and flexible means of tracking epics/features/bugs across an organization, and adoption of the tool came quickly with Rally’s training.

Tom’s tweaks

Our new VP of Engineering, Tom A had come from an Agile background, so he had a lot to say on:

  • the formation of teams
    • a large discusion/debate ensued on the topic of cross-functional teams vs teams aligned with a specific function; in the end, we took Tom A’s approach and created a web team, a backend team, etc.
  • function and composition of Demo mtgs
    • a strong proponent of team’s presenting from a standardized set of power point slides

During Tom’s tenure (8/11 – 1/12), we made several small tweaks along the way. I was still the only project manager, and our Engineering department (including QA) reached approx 25-30 (10 teams) while Tom A was at SendGrid.

Also at this time we initiated weekly Theme Prioritization meetings, a forum for stakeholders to insert and prioritize larger engineering initiatives. Despite it’s shortcomings, we retained this process for over a year as we transitioned leadership a couple times.

Staying the Course with Isaac

After Tom’s departure, Isaac (one of our three founders) assumed VP Eng duties, and Stuart joined SendGrid as our second PM / Agile coach. Having Stuart on board helped me incredibly. We were now able to divide the teams and projects between us, giving attention & coaching much more rapidly.

Stu and I worked with Isaac to deliver a newer set of metrics than what Tom had focused on. We reported things like outages by priority (P1- P4), velocity (Tom also liked this) and percentage of commitments made. On this final stat, Isaac was most insistent. We began asking our teams to explicitly state a list of the stories (and defects, etc) that they committed to getting done.

Also in January, after only six months of using the Rally product, we adopted Pivotal Tracker. Although Rally provided terrific tracking and reporting features, the UX left developers feeling too mired in rules. Pivotal was proposed (Tom’s final push) and was accepted by many (but not all) teams due mostly to its ease of use.

This time I dove in to write a few PHP scripts so we could:

  • perform cross project searches
  • create department-wide cumulative flow charts
  • identify blocked items & dependencies
  • archive retrospective notes, etc.

Agile training, year two

As we approached the summer of 2012 (now one full year in to Agile as our methodology), Stuart and I prepared another round of training for our growing Engineering staff. Although Thomas Peng had recently been hired as VP of Engineering (relieving Isaac), he stepped back to let us administer more-or-less the same training that Ann delivered the year prior. Two days in Anaheim for all Engineering staff, now tipping 30 strong.

One addition to the training agenda was a brief introduction to kanban (from Jim Benson’s fantastic Psychology of Kanban – as Stu & Vic recently attended the summit in San Fran).

Season of Change, 2013

We more-or-less stayed the course for Thomas’ first six months, but with the new year came another opportunity to review and revise the way we do things. Things that we’re currently experimenting with include:

  • Embedding our Project Managers as Scrummasters
  • new Demo Day sked
  • Overlapping Sprint schedules
  • Engineering Retro
  • transition to JIRA (with access to training)

We had a few other events in early January, namely:

  • Management offsite, including a half day with Mike Cohn
  • Product Owner training at Rally attended by Stuart and members of our PO team
  • SendGrid’s 2013 Kickoff in Puerto Vallarta

We also hadn’t held a retrospective for the Engineering department since early October, and we were overdue. (The teams hold their own retros after each sprint.) This time Thomas wanted to make it more of a summit than solely a retro, so we’re scheduling a day and a half affair for late February. Items to include:

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