Empowering IT to Say ‘Yes, and…’: Q&A With JumpCloud’s Tom Bridge
IT services have gone from gatekeepers to becoming enablers within an organization – a shift in mindset from merely rejecting requests or ideas to collaborating and building upon them, fostering innovation and efficiency.
This approach positions IT not just as a support function but as a central pillar of organizational success, integral to driving forward positive changes, enhancing productivity, and shaping a culture of empowerment and possibility.
Optimizing IT resources has become a critical endeavor for businesses aiming to enhance efficiency, reduce costs, and drive innovation. In my interview with Tom Blake, Principal Product Manager for Apple Technologies at JumpCloud, he shares 5 tips for shaping organizational success. From leveraging cloud computing to implementing automation, we explore various techniques to transform your IT operations and propel your business forward.
Thank you so much for chatting with me! Before we dive in, our readers would love to "get to know you" a bit better.
I’ve been at JumpCloud for about two and a half years now, and before that, I spent twenty years between non-profit IT and an IT Consulting firm I founded. I’ve done IT projects for big and small companies, from network and IT systems planning and buildout for a 25,000-person amphitheater to mobile device management (MDM) and identity provider (IDP) selection for a 250-person high-security startup in the energy sector.
I’ve built my career by trying to focus on how IT Services roles stop saying “No!” and start saying “Yes, and…” as they’re the core of an effective organization’s “competency triangle” between Legal, Accounting, and IT Services. Organizations that invest in empathetic and engaged IT teams will reap the benefits of happy and productive coworkers, fewer security issues, and the ability to help shape the culture of the organization in positive ways, and it’s the best lesson I’ve learned about IT’s ability to wield soft power within their organization.
None of us can achieve success without some help along the way. Can you share a story about who helped you and how?
There are three people who’ve moved my career wholesale.
The first is Joel Rennich, VP of Product Strategy at JumpCloud. He and I spent a whole day in front of a whiteboard to explain Users, Groups, Active Directory, Open Directory, Kerberos and Authentication. It was my first complete understanding of a massive technical system, and we went through it in a day. I was absolutely hooked on how these big systems fit together and how they could power new controls for IT without damaging the user experience too much.
The second is Mark Collien, my boss at NCEE as the IT Director and then my partner at Technolutionary. Mark’s focus on serving the person first, their computer second, and the company third was a core foundation of my IT practice. We worked together for the first 20 years of my IT career, and we’ve shared battles, business objectives, and a balancing act for all of it. Without Mark, there’s no way I’d be anywhere close to where I am today.
The third is Erin Merchant, my friend and colleague from the Mac Admins Foundation and an IT Director in her own right at Sidecar Health. Erin’s a no-nonsense friend who will push you to do brave things, tell you where you’re not living up to your responsibilities or your potential, and give you the push you need. She’s one of my ride-or-die friends, an incredible leader, and someone who will tell you to be brave, do hard things, and get massive results. She has been a voice in my head for a long time, pushing me to be better, and everyone needs that in their life.
Let’s talk about how to optimize IT Resources. How do you assess the current state of your IT infrastructure? What metrics do you use to measure its efficiency?
When it comes to key resources, a couple of key indicators of performance (or non-performance!) can be used to measure your resources' value.
The first of these is what kind of support volume a tool is generating within your organization. If you have a tool that is business-critical to your organization but is generating a high volume of internal support tickets, is it still the best tool for your organization?
| Quantifying the “support overhead” for a given tool | Whether it’s your device management solution or a SaaS line of business application, you need to know what is stressing your IT Resources. Building an internal rubric on what you’ll tolerate in exchange for services is essential, especially at renewal time, when you talk honestly and openly about your struggles with a tool. Measure what havoc tools create in your organization as a way of treating that as part of the total cost of ownership. |
| Company penetration a given tool has | If you have license management issues – too many people assigned licenses who don’t use the product, too few licenses for the necessary partners – then there’s an additional overhead on your IT team that is all focused on the overhead necessary to pay attention to these kinds of tools. |
| What kind of feature adoption do you have for tools that you’re paying for? | If you have an accounting solution that does receivables, payables, payroll, invoicing, collections, and auditing, but you’re only using it for receivables and payables, are you using the software to its fullest potential? If not, why not? If not, at what cost? |
Now, all of this is just as applicable to the physical tools that you use - laptops, projectors, and especially, ugh, printers - that you need to determine what’s best on your organization’s growth chart. If you’re stuck on Windows PCs, and they’re hugely problematic for security and usability, considering an employee choice program to adopt more productivity- and security-focused devices like the Mac and iPad, well, you’re going to perhaps lower the cost of supporting your coworkers.
How do you prioritize and allocate resources for hardware and software upgrades to maximize performance?
This is one of the hardest questions to answer because they’re apples and oranges. You need to make these decisions based on the productivity that they provide. If you have a team full of software engineers on four-year-old devices that take a massive amount of time to compile before they can test, moving to new machines will pay massive dividends in productivity, but at the cost of physical dollars.
Most software companies these days have moved to the service model, so there’s no excuse not to stay current, so long as your IT team is working with stakeholders to test new features on new versions of the software. That’s part of your job as IT, though, to stay abreast of developments and focus on the needs of your coworkers, so that part should be de jure within your area of responsibility.
In short, maximize for your teams’ productivity, and know that refusing to stay current will have costs related to your coworkers’ comfort, productivity, happiness, and engagement with their team. Moving to shorter refresh cycles can help your finance team by moving to leasing devices or even to deeper discounts with equipment manufacturers.
What security measures are in place to safeguard your IT infrastructure while optimizing its performance?
Communication is at the center of every IT Services team. If you’re not talking about what you’re doing with your coworkers and you’re working in a silo, changes to the environment are going to be challenging for your team and your organization as a whole. Taking appropriate change management controls into account as part of your security measures will give you clear sequencing of changes, as well as team and company-wide visibility for what’s changing.
Having an open process that anyone from the CEO to the front-line worker in your organization can see and understand is crucial to the success of this effort. Good change management will save you from yourself. Bad change management, though, will not optimize your performance.
How do you identify the skill sets and competencies required for your IT team to effectively manage and optimize resources?
Building a team with the right skills and knowledge is an exercise in determining outcomes for your IT team. Do you need a networking team if you don’t have an office? Mapping out what you have to support versus the skills and knowledge required to support it is IT Director 101. If you don’t have the right skills, it’s as much an item for your risk register as not requiring operating system patch management or providing admin rights to every user in your organization. Make a list of everything you own, all the orthogonal support skills required, and map it across your team. Don’t have what you need? Time to invest in professional development or a new team member.
What strategies do you use to foster professional development and continuous learning within your IT team?
There’s a saying that applies just as much to IT as it does to Product Management: “Never, ever waste an escalation.” What that means for IT is that any crisis your team faces, any sufficiently developed problem, is an opportunity to grow, learn, and change your priorities. Got a security situation? This is a great way for new people in your IT team to be part of the process and learn from the primary actors in your organization for security. Got a deployment opportunity? Let’s be more cross-functional and get more people involved.
More than that, writing after-action communication, training materials, and retrospective meetings to cover what went well, what needed work, and where you didn’t have what you needed is a critical opportunity for any IT team to grow and learn.
How do you identify bottlenecks or inefficiencies in your IT processes that might hinder resource optimization?
Any process that requires more than one handoff is probably inefficient in some capacity. If you must go between telecom, networking, security, and help desk in a single ticket, you likely have a more complicated processing system than you need.
Plus, you have to consider how the affected party – the one who brought you into the situation in the first place – will feel about being passed from point A to point B through D to have their problem resolved. It will feel like a simple problem to your coworker who is affected, why shouldn’t the resolution feel as simple?
Oftentimes, siloed knowledge will result in delays and bottlenecks when the person with all the knowledge is on leave or out sick. Shouldn’t you have a way to avoid that kind of critical blockage? We trade in redundancies in IT – battery backups for power, geographic diversity for data centers, multiple internet connections for throughput – shouldn’t we do the same for IT processes? A department that isn’t harried for resources and has adequate backup is ready for a full-scale crisis in a way that one that is under-resourced and under-trained will never, ever be.
How do you ensure that your IT processes are aligned with business objectives and contribute to overall organizational efficiency?
IT is a force multiplier for your other teams as part of the Competency Triangle, and that means that your IT folks need to streamline the amount of downtime their coworkers face based on the resourcing required.
What are your 5 tips for shaping organizational success with IT?
1. Focus on what’s necessary first. You don’t need every line of business application or software as a service product to be the best within the top corner of the Gartner quadrant. You have to balance your cost exposure with the functionality needed for your business, all aligned with your needs for security and supportability. Picking the right product based on a balanced approach or using a product you’re already paying for with new functionality within the platform is a crucial part of managing your resources.
Picking the absolute best product every time will lead to management creep, division of resources across too many platforms, and a staggering IT budget – all for, what, a 2% increase in productivity? Balance is best.
2. If your IT team isn’t part of the business’ solution, it’s part of the problem. From the perspective of your coworkers, if IT is considered part of the organization’s competency triangle, you’ll be part of the solutions they bring to market. If you’re thought of as a place where good policy goes to die, or where process overwhelms good judgment, or where the team is focused only on the machines and programs and not the people using them, then you’re going to be routed around like damage.
Focusing your efforts outward within the organization, and even having a product manager as the frontline face of IT within the organization, is a key way of making IT respected and part of the solution the organization represents to your customers.
3. Have enough capacity for rest. Every organization is working to be as lean as possible, and that’s certainly understandable given the economic conditions these days, but if you are running such that any vacation, any sick day, any sick kiddo or parent causes an abrupt halt to your operations? You’re running too close to the bone. You need your staff rested for the big games – security events, migrations of platforms, and big conference events – and that means having enough capacity to cross-train, enough planning to allow for leave in your key personnel, and enough development time to represent key solutions to your internal and external stakeholders.
If you don’t have that capacity, you’ll burn your people out, and you’ll have to hire more of them, train them, and get them up to speed. Plan for the future where you have adequate staffing to handle your growth, not a lean-and-burnt-out IT team.
4. Don’t keep poor performers on and expect them to change. Look, the scariest response to “What happens if Person A leaves?” is “What happens if they don’t?” If you have people on your team who are challenging to train, keep motivated, or keep engaged with your organization's mission or are toxic for your team, you need to do the hard thing and let them go. There is no excuse for keeping someone who doesn’t fulfill their obligations. It can be scary, but you need to do the right thing for your organization sometimes. Be compassionate, offer clear feedback and a letter of recommendation, and then set them free. It’ll be okay.
5. Look forward as much as you look backward. This one is simple: some organizations choose to live as if their past actions have no consequence on their present, and some organizations choose to believe that their future is impossible to predict, understand, or plan for. You have to spend equal time thinking about what’s worked over the last year or longer and what’s coming at you in the future. Don’t pretend the one you don’t like hasn’t existed.
Is there a person with whom you would love to have a private breakfast or lunch, and why?
I’d love to spend a morning talking strategy with Billy Beane of the Oakland Athletics. His work with Moneyball transformed a franchise with a limited budget and big dreams. There’s no question that the effects it had on baseball writ large were substantial and changed the face of the game. What would he change? What would he do differently? What would he do less of? These are the questions that I spend a lot of my time thinking about as I consider leadership and strategy at Jumpcloud.
Thanks for your time, Tom!
Venturing into the world of information technology might feel like you've been dropped in a digital jungle without a map. Books about IT and firsthand knowledge from leading experts are great resources to help you navigate. If you'd like to read more of our interviews, please subscribe to The CTO Club newsletter for the latest insights from your peers.