The Contractor Conundrum: 5 Lessons to Speed Up Your SaaS Roadmap Without the Headaches
I’ve hired 50+ contractors across multiple companies globally. Here are five lessons I’ve learned that will save you time, money, and headaches.
It’s a tale as old as time. Your roadmap is packed to the brims, and your full-time staff can’t keep up. So you hire contractors to fill in the gaps and accelerate development. They’re going to integrate quickly, get right to work, and move twice as fast as your full-time team.
Right??
Whether you’re at an enterprise company or own a business, hiring contractors can be an effective strategy to deliver your roadmap quickly – and at a fraction of the cost. But if you’re not careful, the time spent onboarding, training and integrating will cost you more money, not save it.
1. Be realistic about scope and timeline
I have seen many instances of “rolling” contractors – ones that stay on indefinitely. In early-stage SaaS, this can be a smart way to move quickly. But as your company scales, relying on contractors long-term becomes less effective unless there’s a specific, time-bound project.
Think in terms of outcomes: delivering a feature that requires specialized skills, implementing a global design system, or handling a one-off customer project. Be honest with yourself about whether your project is time-bound or looser. If the need is open-ended, it’s better to invest in a full-time hire who can grow with the team.
2. Build an onboarding plan that saves time, not wastes it
We’ve all been on the receiving end of a bad onboarding: no logins, no guidance, and the immediate “wtf am I doing here?” moment. With contractors, that wasted time is even more expensive — every hour of ramp-up costs you more than it would for a full-time employee.
Be prepared for their first month: why are they here, what are their goals, which tools do they need, which resources should they review, and who should they meet? A clear plan saves you headaches and gives them the context to contribute faster.
And remember, contractors aren’t forever. Just like an FTE, you want them to leave with a good impression. Poor onboarding not only hurts output but can also damage your reputation — with recruiting agencies, referrals, or even Glassdoor reviews.
3. Embed contractors into your culture
If a contractor is hired for a short-term, specialized project, it makes sense to keep their exposure limited to their direct team and manager. That keeps things simple.
But if they’re working alongside full-time team members, isolation becomes a risk. Excluding them from meetings, town halls, or team chats may save money in the moment, but it may also cut them off from critical context. They may miss details which the rest of your team may have, leading to confusion and inefficiency.
If contractors are expected to collaborate closely with your team, two things are essential:
Give them the same context as everyone else — strategy, priorities, and approach.
Create opportunities to build rapport, since relationships often drive execution. This becomes especially important in remote environments.
This investment pays off in stronger outcomes, smoother collaboration, and more buy-in.
4. For more junior contractors, consider investing in their development
This one may be controversial. Most people hire contractors assuming they don’t have to deal with “the HR stuff,” like performance management. And yes, that is partially true. Seasoned contractors are compensated well and usually require limited coaching or oversight (assuming you nailed #1 and #2!)
But if you’ve consciously hired someone junior – maybe for budget reasons – it’s worth investing in coaching and upskill. Evaluate them for the role you need, but be realistic about potential gaps. If you transition them to a full-time role later, you’ll already know they’re coachable and capable of growth.
If you don’t have time to coach, reconsider hiring anyone with less than 5–7 years’ experience — unless someone else on your team has the skills and interest to step in.
5. Tie contractors to outcomes, not hours
The fastest way to waste money on contractors is to treat them like task rabbits. Instead, set clear outcomes tied to business value — revenue, customer experience, or reduced cycle time. When contractors understand the “why,” you’ll get higher-quality work, not just more output.
Because contractors may naturally be more isolated than your full-time team, it’s your job to make sure they know why they’re here, what success looks like, and the milestones they’re driving toward. Clear, measurable objectives keep everyone aligned.
And honestly, this applies to all hires — not just those under contract.
Closing thought
Contractors can absolutely speed things up. But only if you set them up right — with clear scope, a real onboarding plan, cultural context, and goals tied to outcomes. Do that, and they’ll drive impact. Skip it, and you’ll burn time and money.
