Robert W. Dempsey


Proven Engineering Leader. Author of Python Business Intelligence Cookbook (Packt).

rd-profileA tested leader and technology professional delivering solutions and products to solve tough business challenges. My experience forming and leading agile teams combined with more than 17 years of technology experience enable me to solve complex problems while always keeping the bottom line in mind. I have founded and built three startups in tech and marketing, developed and sold online applications, consulted to Fortune 500 and Inc. 500 companies, and spoken nationally and internationally on software development and agile project management.

Core Competencies

  • From-the-front leadership and mentoring
  • Project planning, execution and measurement
  • Infectious positivity – but not to the point of being annoying

Technology Expertise

  • Microservices architectures and API development
  • Cloud services particularly Amazon Web Services
  • Distributed data gathering and processing systems

Items of Particular Note


Profesional Experience

Snagajob – Principal Architect

03/2017 – 09/2017

As part of the Relevance Team within the Match Tribe I am leveraging Python to rewrite our existing job search platform, converting it from Solr to Elasticsearch, in order to utilize machine learning techniques to improve the search experience for hourly job seekers.

Notable achievements include successfully completing and launching a data processing pipeline into production within my first 30 days of employment. In addition, I completed ElasticSearch Core Developer training and have been performing internal training for the team.

IST Research – Lead Systems Architect

02/2016 – 03/2017

Architected, developed, deployed and maintained fully distributed systems to collect, process, analyze and visualize combined offline and online data in real-time. Collected data from the public web, dark web, social media sites, SMS messages and other sources using a combination of technologies including Python, Redis, Kafka, Elasticsearch, Logstash, Kibana, Docker and Ansible.

In addition to providing mentorship to other engineers I helped combine two silo'd engineering teams into one, implemented combined grooming, demo and planning meetings, and led daily scrums.


ARPC – DataOps Team Lead

11/2013 – 12/2016

Originally hired to do inbound marketing for a new product, my role has changed since starting at ARPC. My current duties:

Data Operations

  • Data operations team lead
  • Set up an automated reporting solution utilizing Python, LogStash, ElasticSearch and Kibana, hosted in a secure Amazon Web Services environment
  • Implemented predictive modeling to improve a critical claimant verification process
  • Implemented Pentaho Data Integration (PDI) for ETL
  • Spearheading the migration of our Claimant Information System – a data wrangling and analysis system allowing us to match data (demographics, lawsuits, liens) to individuals – from Microsoft SQL to MySQL. The system is secure, cloud-based, almost 100% automated and has private APIs.

My past duties have included:

Project Management

  • Leveraged my local tech connections to build a Ruby on Rails team to develop a new product.
  • Managed the team that I helped build: 6 developers, 2 designers, 3 user acceptance testers.
  • For my team members: established expectations, conducted monthly one-on-one sessions, performed yearly performance reviews.
  • Perform ongoing recruitment to add additional team members for every area of the department.
  • Developed and maintained a system to automatically track and classify all materials around the product: documents, emails, images, etc.
  • Augment our Kanban board with a custom application designed to garner more metrics from our project.

Marketing, Sales and Support

  • Created and implemented an inbound marketing strategy for a new product, using HubSpot.
  • Performed product demos for prospects and training for clients.
  • Provided phone and Internet-based support for users of the product.

Intridea, Inc. – Director of Engagement

4/2013 – 10/2013

As the Director of Engagement at Intridea, I reported directly to the CEO. I was responsible for the establishment and management of a marketing funnel including the creation of mail, email, and social media campaigns; identifying, scheduling, and participating in conferences and meetups; establishing and managing a sales pipeline; and identifying and closing services opportunities from that pipeline.

As a growth hacker, I continuously analyzed the key metrics of the company using code I wrote, and worked to improve them. The tools I used are Ruby, Python, R, and Tableau.

I built a system of client and prospect intelligence using a combination of Ruby and Python, taking advantage of social media (Twitter, LinkedIn, Facebook, etc.) to monitor everything said by and about our clients and prospects.


  • Sponsored and attended 9 Ruby and Design conferences throughout the United States
  • Attended more than 100 meetups covering Ruby, Python, data, design, MongoDB, Node.js, and the Internet of Things
  • Spoke on building a client intelligence gathering system at Arlington Ruby, Big Data DC, DC Python, Data Science DC, and the DC Tableau Workshop

Dempsey Marketing – CEO & Founder

12/2010 – 4/2013

We help service-based companies grow their businesses by connecting with their ideal clients – the people they most want to work with – on a deeper level through strategic online marketing and relationship building.

As the CEO of Dempsey Marketing I’m responsible for top-level strategy creation, business development, process creation and improvement, and just about everything else a growing business requires.

We specialize in two areas:

  1. Lead Generation Websites
  2. Trifecta Marketing Campaigns


  • Worked with the VP of Marketing at The Canfield Training Group to produce the new website
  • Helped Pete and Dean of SagePresence achieve 3, #1 rankings on within 48 hours of the launch of their book – Winning Presence for Business Presenters
  • Built the company while living with my family in Chiang Mai, Thailand

Gunner Technology – VP Client Marketing

01/2012 – 03/2013

As VP Client Marketing I increase traffic and business to and from clients’ properties, including websites, web apps and mobile apps, through:

  • Campaign creation, planning and implementation
  • Social Media Marketing
  • Search Engine Marketing
  • Ad creation and management through AdWords, Facebook Ads and more
  • Analytics monitoring and reporting
  • Content planning and creation
  • Content Submission
  • Directory Submission

In addition I collaborate and consult with the mobile development, web application development and web platforms teams to get it done.

Life of the Freelancer – Chief Freedom Officer

07/2010 – 02/2012

I teach people how to apply the freelance mindset and learn the business skills necessary to thrive in the new world of work, where everybody is a freelancer.

Within 3 months of launch, I hit the front page of Google, hosted over 420 Facebook Fans, 1000+ daily visitors, over 1200 RSS Subscribers, and more than 2000 iTunes subscribers. I also conducted more than 200 video interviews with entrepreneurs throughout the United States and Asia.

Atlantic Dominion Solutions – CEO & Founder

2000 – 04/2011

Responsible for product management, project management, development and execution of marketing strategy.

  • Successfully developed and launched a product portfolio of 3 SaaS-based applications.
  • Performed market research to develop and formulate a successful social media strategy.
  • Developed and maintained online support communities for each portfolio application.
  • Managed a core team of Ruby on Rails developers and graphic designers, and a geographically distributed outsourced team.
  • Implemented Agile practices including Scrum, Test Driven Development, and Continuous Integration
  • Implemented Lean software development practices to reduce operating costs and improve team performance.
  • Increased community involvement by organizing meetups, sponsoring local tech events including BarCampOrlando, and a two-day developer conference 2 years in a row.
  • Published weekly articles about Agile topics on website and blog, and developed Agile training videos.
  • Held the Agile Meetup for 1 year, a well-attended monthly where the group is presented on a specific Agile topic and then holds a facilitated discussion.

Client Work

  • Worked with more than 25 clients to develop requirements and functional specifications
  • Successfully launched more than 25 internal and web-based applications for clients in industries including automotive, publishing, insurance, non-profit, social networking, and more.
  • Developed product roadmaps with more than 25 customers.
  • Identified key metrics, reports, and performed analysis to measure the effectiveness and success of all client projects.

ASysTech, Inc – Project Manager

2006 – 2007

ASysTech has been servicing Central Florida since 1992, and provides clients with a wide range of technology-based solutions including managed services, network design and administration, and computer hardware and software.

As a project manager I managed a team of six systems engineers, and worked with customers to develop, implement, and support custom technology solutions.

  • Planned and implemented the “MBA” program, a managed services offering using Kaseya
  • Managed a team of systems integrators and consultants
  • Helped asses client hardware and software needs for Microsoft Windows networks, including the Internet connections to the workstations and everything in-between
  • Planned and executed large-scale integration projects for clients with single and multiple locations
  • Planned and executed infrastructure upgrade projects
  • Implemented LeftHand Networks SAN storage into existing client infrastructure
  • Implemented server virtualization for clients using VMware and Microsoft Virtual Server
  • Implemented Neverfail as a solution for continuous availability, disaster recovery, and data protection
  • Integrated SpectraLogic backup solutions into existing client infrastructure
  • Maintained vendor relationships
  • Obtained the Neverfail certification in addition to my existing LeftHand certification

Canin Associates – Network Administrator

2005 – 2006

Canin Associates is a 65-person, 26-year old interdisciplinary firm of idea-based professionals committed to creating sustainable resort and mixed-use communities that enrich the quality of life and are wonderful places to live, work or visit.

As the network administrator, I was responsible for management of the IT department, server and client maintenance, and all end-user support.

  • Implemented a LeftHand SAN solution halting all downtime due to storage limitations, saving the company thousands of dollars per hour
  • Planned and implemented the network design
  • Created the IT Department budget
  • Provided end-user support
  • Maintained the server infrastructure
  • Sourced and procured all computer and network hardware and software
  • Worked with third-party vendors


Rollins College – Crummer Graduate School of Business

2008 – 2009

MBA , Business Administration

Rollins College

2005 – 2007

B.A. , Computer Science

Valencia Community College

2002 – 2005

AA , General Studies Phi Theta Kappa

Board Memberships and Organizations

District Data Labs – Faculty

05/2015 – 12/2016

I deliver data engineering workshops to students both online and in-person. Topics include ETL for data analytics, web scraping, centralized event processing, relational and non-SQL database setup and management, data modeling, infrastructure deployment and management, and more.

In addition I co-manage the Data Science Project Incubator, a structured 3-month project development program where teams of people located in the Washington DC metro area work on data projects together. As co-manager I'm responsible for the operations of the program, as well as mentorship of the teams for their project and presentation work.

Data Community DC – Board Member

12/2013 – 04/2016

Board member of Data Community DC, an organization promoting data and statistical sciences by supporting Meetup events and other initiatives.

Data Wranglers DC – Founder & Organizer

12/2013 – 04/2016

80-90% of time spent on data projects is gathering data and putting it into a format you can analyze. Data Wranglers DC is a professional group that meets monthly to discuss topics including open data, data gathering, data munging, and the creation, storage and maintenance of datasets. We combine presentations with hands-on workshops, always seeking to make our data munging lives easier. No experience necessary – just bring your interest.


  • Big data
  • Analytics
  • Predictive Analytics
  • Statistics
  • Data Mining
  • Robotics
  • R (programming)
  • Python
  • Military Strategy
  • Military History
  • Intelligence


Certified Scrum Master


Scrum Alliance

Kanban Coaching Professional


Lean-Kanban University