The First 100 Days: A Leader’s Guide to Digital Quick Wins.

Stepped into your new leadership role?  

You’ve likely inherited legacy platforms, a loosely tethered mesh of platform affinities, and some strategies, that with a fresh set of eyes, appear patchy. 

Of course, you are here because the Board is keen to see positive impact. 

Everybody understands that transformation takes time, but we all also know perception matters. Those early wins are all important, they build credibility, they start to create that momentum, and they clearly signpost that the direction of travel is upwards. 

The first 100 days are as much to do with showing meaningful progress and building trust, both at board level and with your stakeholders, as they are about fixing the underlying problems. 

So you’ll want to focus on the right quick wins, not just the lowest hanging fruit. 

The first 100 days aren’t just about fixing problems. They’re about showing meaningful progress and earning trust, both at board level and across your stakeholders. 

This guide focuses on the right quick wins - the ones that create real momentum, not just easy fixes. 

What you’re likely seeing 

The first few months in any leadership role feel like they disappear remarkably quickly, but the strategic objectives are a long way off.  

You may be facing: 

• Pressure to perform: Organisational leadership always hunger for evidence of positive change. 

• Lack of clarity: Existing roadmaps or shared vision may be lacking the current context and may carry a degree of debt (technical or emotional). 

• Team fatigue: The people you’re relying on may be tired, sometimes of “constant change”, or sometimes from the lack a refreshing one.  

• Mixed signals: Some stakeholders relish change. Others the status quo. Some will not commit. 

Your job within transformation is to create clear consensus, to define strategy, and to assess and address resource limitations. 

You know you don’t need all the answers today. What you do need is a focused plan for your first 100 days. 

Your 3-phase plan for digital progress 

Days 1–30: Listen, learn, light the way 

Goal: Understand the current state and shape your point of view. 

• Audit the digital estate: What tools and platforms are in use? What processes are they supporting? Where, in all of this, is the friction?  

•  Identify the blockers: Is it tech, people, politics - or a nuanced combination of all three? Are your people processes and platforms working in sync? 

• Enable honest input: Speaking to internal stakeholders, front-line teams, and most insightful of all, your customers, your experience here will shape the future. 

• Set your digital ‘North Star’: Create that compelling vision that can anchor future conversations. But most importantly, set an achievable direction.  

What to share: A visual snapshot of “What we have now vs. where we want to be” - lightweight, but clear. 

Days 31–60: Prioritise, pilot, prove 

Goal: Start small but strategic, proving value but not yet achieving perfection. 

•  Pick your short list of ‘quick win’ projects: Choose initiatives with clear provable ROI or internal benefit - form simplification, reporting automation, CX pain-point removal. These changes can often be achieved quickly using known best practice, reducing the timelines to an outcome. 

• Prototype - don’t over-plan: These should be experiments, not commitments. The objective is to validate a piece of the plan or fail quickly, delivering hindsight fast.  

• Establish your governance model: Lay down your appropriate rituals - periodic check-ins, visible Kanban boards, or sprint reviews. 

• Track and share outcomes: Small metrics (time saved, user satisfaction, response speed) matter at this stage. There are learnings and successes. All build on the sensation that things are moving. 

What to share: “Here's what we changed, why it matters, and what we learned.” 

Days 61–100: Build the case for the future 

Goal: Translate early momentum into a structured roadmap - and lay the groundwork for more ambitious change. 

• Create a Now / Next / Future roadmap: Your early wins illustrate how change will be delivered incrementally. 

• Begin platform discovery: You are now clearer on how your tech is supporting your processes.  Where tech is the bottleneck, you have a clearer knowledge of what’s holding you back - and what needs to change.  

The marketing platform landscape is complex, and what may have served well in your previous roles may not be what will solve your current challenges. It’s not uncommon for a great platform to be made impotent by an implementation that doesn’t support the real challenges of an organisation. 

• Engage the wider leadership: Using evidence from early wins to have constructive conversations about investment, timing, and appetite for risk. Platforms will carry dependencies and data and processes that are owned and supported by other groups.  

• Decide on your next 90–365-day focus: Keep things moving. Conclude your 100 days with clarity about what comes next and where that will take the organisation. Establishing a clear view of not just the investment and resources but the technology and digital tooling that will create the commercial difference.  

What to share: “We’ve built momentum - here’s where we go from here.” 

Quick wins that work (real-world examples) 

Not sure what to prioritise? These types of projects deliver visible results and build trust fast: 

• Fixing a broken or outdated contact point. Address any forms or mechanisms that cause customer friction. Turn digital touchpoints into tangible business data - data that helps you better understand your organisation. 

• Introducing a dashboard. Align clean data with a format that speeds up decision making and replaces clunky spreadsheet reporting. 

• Digitising paper or longwinded manual processes used by internal teams. This can increase capability or speed of delivery. Look at end-to-end processes like your content lifecycle, or marketing optimisation process. 

• Re-platforming a microservice that's causing operational risk or disrupting a significant customer flow. 

• Piloting a new customer feedback loop with simple UX tools. Targeting gaining specific insights that will inform next stage enhancement.  

Targeted changes demonstrate that problems are diagnosed correctly and getting on the road to resolution. 

The power of framing 

How you communicate progress is as important as the progress itself. 

Focus on benefits, not features: “We saved 6 hours a week,” not “We used a new tool.” 

Use simple visuals to show movement over time. 

Talk to collaboration, not disruption: “This made the team’s day easier,” not “We’re transforming the workflow.” 

Where support can accelerate your impact 

You can - and will - drive this yourself. But these areas are where external input can help you go faster and further: 

• Road mapping: A short engagement to shape your “Now / Next / Future” vision with external validation. 

• Platform Discovery: A focused review of how your current tech stack is enabling or blocking your achievement of goals. 

• Board Engagement: An external perspective can help align your C-suite on vision, risk, and investment. 

This isn’t about bringing in lots of consultancies - it’s about getting you unblocked and in motion. 

You’ve got this - and you’re already ahead 

The first 100 days are a launchpad, not a finish line. 

You don’t need a revolution. You’re starting to set the rhythm. 

Want a head start? 

Contact us to explore our roadmap & platform discovery services, designed to help digital leaders clarify, prioritise, and get unblocked - without long-term consultancy.