In this 10 questions article, we talked to Ashley Wiltshire, founder of Wiltshire Paraplanning, about setting up and running an outsourced paraplanning firm for over 11 years, what her experiences have taught her, and what she might do differently if she were to set up her business today.
1. What made you want to set up your outsourced paraplanning firm?
Initially I was joining another company to work with, which was great to start with, but I fell into working on my own. Initially I didn’t have any big plans and thought I would paraplan for a couple of advisers that I knew. However after having a conversation with one of my mentors at the time, they suggested finding other paraplanners to work with me and to start contracting work out that way. I think it was at that point my entrepreneurial mind began!
2. How has your firm changed between set up and now?
It started with just me, but my pivoting point was when I took on my Office Manager Charlotte, as together we were able to take on more advisers and contract out more work. Now I have 4 employees and a couple of subcontractors.
3. What one thing would you have liked to know before setting up?
Oh gosh this is a hard one! There are so many things you learn along the way but I would say from a practical perspective making sure I am using an accounting system from the start, so it makes doing your taxes A LOT easier.
4. What industry change is most affecting your business, outside of regulation and legislative changes?
AI! You need to keep pace with the changes or you will be left behind!
5. What has been your greatest challenge experienced in running your own firm?
a) Professionally: Capacity management. Balancing quality with volume is always tricky. Bringing on help at the right time, training well, and trusting others to deliver to your standard is a constant balancing act.
b) Personally: Switching off and not taking things personally – It took me a while to build boundaries that protect my energy and mental health.
6. Do you think it would be harder to set up an outsourced paraplanning company now than when you did it?
Yes and no. There are more tools and communities now to support new paraplanners, which is great. But expectations are higher, and competition is stronger, so you have to be crystal clear on your value and offering from day one.
7. Where do you see the challenges for outsourced paraplanning going forward?
The challenge will be staying relevant. As some advisory firms move elements of the advice process in-house again or lean more on automation, paraplanners (in general) need to bring more than technical accuracy – they need to be strategic, proactive, and truly understand the client outcomes.
8. Where do you see the opportunities?
Advisers are under huge time and regulatory pressures – if you can find a specialisation to support this then you are adding value where it is needed.
9. Talking specifically about AI, how are you approaching its onset into paraplanning?
I see it as a tool, not a threat. Used well, AI can speed up mundane tasks and provide opportunity for further growth. But the value we add is still in understanding nuances, making judgment calls, and communicating complex advice clearly. I’m already integrating AI to support efficiencies, but with a very human final layer.
10. If you were setting up from scratch now, is there anything you would do differently?
Spend time on thinking about what systems I could use to make me more efficient with my time and using automation as much as possible. I would also look to work with others like me so I could build confidence in all things paraplanning. That experience is exactly why I now offer coaching for paraplanners.
I offer five 1:1 coaching slots each week, which can be booked as often needed. For those not quite ready for one-to-one support, I’m also planning to launch a weekly group call – a more accessible option that still offers guidance, connection, and accountability.
If you’re a paraplanner looking to strengthen your business, gain clarity, or simply have someone in your corner, I’d love to hear from you: [email protected]
