Inspiring Business Women: Shelley Grayson

​​​I recently had the great pleasure of interviewing Shelley Grayson, the Head of Compliance at FinTech start-up LiveMore Capital. We spoke about her career journey so far, and the obstacles and challenges she’s had to overcome to get to where she is today.

​​Shelley, can you tell us a little about your career progression to date?


I have had a rollercoaster of a ride! Having left school with no qualifications, I only wanted to be a DJ so set off on that path (including six months on a pirate radio station). Working multiple jobs such as a secretary, waitress, translator, and sales rep, I eventually ​found my

niche in the insurance world. I studied really hard for the CII exams and then went on to qualify in law aged 33. I have not stopped academic pursuit since, and I’ll often do an online qualification when on leave. I did the New York State Bar MPRE in 2017, GDPR certification in 2018 and last year I passed Level 1 Mandarin.


At work, I loved being able to provide perfectly bespoke products to respond to peculiar needs and there began my geekiness in getting technical with coverage and claims. This landed me back in the UK in the centre of the world’s insurance market selling to and servicing telecoms and tech clients from all over the world. From there I moved across from insurance to bancassurance, banking to finance, then back to private banking and three decades later, I am now Head of Compliance for a really exciting FinTech start-up called LiveMore Capital.

What key factors propelled you to enter the Compliance space?


I had worked in business development for well over a decade and saw how much my clients loved having a technical approach to their coverage and a relationship built on clearly articulated needs being met. Technical prowess wasn’t something which the sales teams saw as being a big deal, so Compliance became a natural home for me to enable business through compliant and yet very creative solutions. I quickly realised I wasn’t thinking like other business development team members, but I also recognised this difference in view and approach brought an additional layer of value and integrity into what had previously been a rather one-dimensional approach. The transition was mostly through my own efforts, volunteering for projects and voicing thoughts frequently and constructively around compliant provision of new services or products. The balance slowly tipped until about ten years ago, when I totally left the business development space and emerged full time in Compliance.


Moving into my current role at LiveMore was a no-brainer because I am passionate about the mortgage market working better for consumers, especially mortgage prisoners. There were many other factors to choosing this move, including a high quality team of peers with lots of energy, 21st century tech, broad and deep responsibilities, it counting when you work or don’t work, and a passion for building a new business. Also, I had reached a point where having a dog in the office sounded like such a great idea, I wanted to go to a workplace where that was cool. (LiveMore has an office dog – woofs!).[

Having worked across a variety of roles within Financial Services, what challenges did you experience moving across to Compliance?


I have seen some organisations seeking only experienced hires for brand new regulation. That’s frustrating and means companies are confined to a very limited talent pool. I have had to persuade my employers around skills which are analogous and can transfer across disciplines to make any breakthroughs; identification of raw skills which are suited, like natural curiosity coupled with technical audit and paralegal or investigative disciplines make for energised, fresh and agile hiring takes a lot of persuasion.

What are some of the biggest challenges you've faced in your career so far, and are any due to gender?


The greatest challenge I have faced in my career so far is learning how to change attitudes in businesses who view Compliance as “the department of business prevention” into businesses who view Compliance as enabling better, fairer and more sustainable business. When done right, and creatively, Compliance can always give competitive advantage to any business.


I have felt gender imbalance over my (quite lengthy) career; automatically being paid far less as a base salary, receiving lower bonuses, seeing eyebrows raised when I announced I was pregnant or rush off to a kids arrangement, coming back to work after kids on a lower salary and less responsibility, my managers having lower expectations of me despite me still loving what I do. When I was given a secondment to the Far East for two years, my boss actually asked me to not get pregnant (I was newly married) as, in his words, that would be career suicide for me.

Do you believe there's a glass ceiling for women in the workplace, and has it changed?


I believe there are a number of “glass cliffs” for women which still take a higher degree of performance to scale. In the Big 4, my experience of the women I engaged with who made it to partner so very often appeared to do so by being “one of the guys”. I chose a different path, and I have no doubt it has meant a slower and more gentle career climb, but staying authentic to myself and reaching a healthy work-life balance still feels to me like I made the right choices.

When it comes to diversity, how do you feel that the Financial Services industry compares to others, and how has that changed?


It is constantly improving, but from such a low starting point that is still not setting the bar very high in the UK and “old Europe”. Newer and more dynamic economies like South East Asia and Eastern Europe have more women in senior positions and a clearer focus on diversity values.


FinTechs like LiveMore have a clean slate – we actively focus on diversity because it makes sense for us, ethically and commercially.

Looking back on your career, what are some of the key moments that have helped or hindered you in getting where you are?


I messed up once, big time. It was the best learning experience I ever had. I was humbled, needed to reflect on what went wrong and fully own the consequences. It was very hard at the time. Now I look back on that inflection point and how it forced me to face up to who I was and what I wanted to be. It brought integrity into central focus for me and that has defined my career ever since. What has helped and hindered me most at the same time is my desire to remain authentic. I am naturally very nosy, very bubbly, very competitive and ridiculously positive – that can be annoying for others and I have to remain conscious of that, without becoming flat and less passionate. I’m now at an age and in a position where being authentic is more of an advantage as it is supported with knowledge, maturity, empathy and a bit of wisdom.

What advice would you give to a woman looking to progress their career in Compliance?


Do it. Get qualified in some credible areas, seek a mentor or two who you can help so they can help you, always be on the lookout for opportunities to provide a range of solutions other than “no”. The intellectual stretch is there every day if you assume “no” is not an acceptable default position for any Compliance response, and you will build a position where you are fundamental to the success and culture of any financial services business.


A few last golden nuggets of advice I would also add are:


  1. Be kind and helpful. Always. To everyone.
  2. Never say anything behind someone’s back you would not be ready to say to their face, but when it needs saying, absolutely say it.
  3. Always be sure of your facts, and if you’re not, say so, preferably in advance.
  4. When you interview somebody or provide an appraisal, whether they are successful or not, be clear in providing constructive feedback and recognise their life is literally in your hands.

A huge thank you to Shelley, for opening up about her own journey to where she is now. If you, or someone you know, is an Inspiring Business Woman in Compliance, and has a great story to tell, then I’d love to hear from you! Contact me at danielbloom@hydrogengroup.com.

26 Feb, 2024
​Our webinar 2025 and Beyond: Why Your Hiring, Learning, and Culture Need to Evolve brought together thought leaders Enrique Rubio (Hacking HR), Lisa Skinner Källström (Teamtailor), and Hydrogen Group’s Dean Jennings and Michelle Miller. The conversation explored strategies used to tackle the challenges of the future workforce, shift organisational cultures towards lasting partnerships, and ensure teams are equipped for the age of artificial intelligence. _ The Q&A box was brimming! Our webinar offered participants the chance to consult our HR experts on addressing shifts in the people and culture realm as we approach 2024 and beyond. Interesting questions were raised, and we compiled them all to seek and reached out to our experts to get some definitive answers. For a recap on the webinar, check out our blog Navigating the Future: Insights from our Webinar "2025 and Beyond"  So, here we are. Your questions - answered! - ​How can companies make people feel more secure in their jobs? Is it just a matter of increasing communication? Lisa suggested a shift towards a more sustainable approach. 'In recent years, we have seen many companies experience massive growth, and the need to get great talent onboard - hence offering extremely generous compensation packages. Unfortunately, many have now faced layoffs, and while the compensation and benefit strategies are not the sole reasons, I would like to propose a more sustainable approach for the future. [Increase benefits as the company grows, and as business results allow, we can increase pension levels or similar benefits – and discuss it internally! Open dialogue about results, investment choices, and their rationale fosters a sense of involvement among team members and signals the company's commitment to a sustainable direction.]' Dean echoed concerns about job security in today's volatile economy and advises, 'In today's uncertain economic climate, job security is a concern. However, by becoming indispensable and embracing tools like AI, individuals can enhance their value to employers, securing their positions for the future. Apart from using Chat GPT, what other tasks can be automated with AI? Lisa commented, ‘We’ve mentioned a few examples already, but I would look at all the systems your company allows you to use and question your suppliers on what features are or will be based on AI. For example, many applicant tracking systems allow the opportunity for AI to summarise CVs for an easy overview, generate interview questions and suggest more personalised replies to rejected candidates based on their CVs. Also, the opportunity for AI to transcribe an interview is an amazing tool which allows the interviewer to solely focus on listening and talking to a candidate as opposed to taking notes. As always, AI in these types of systems is not designed to make the decisions for a recruiter or business - but serve as an assistant to save time and work more efficiently.’ Dean added, ‘There are far too many to list. The AI directory https://aitoolsdirectory.com/ does a really good job of showcasing what does what and where you can find it.’ What is the impact of AI on employee engagement and how can HR teams use AI to promote engagement? Also, what precautions should professionals take when using AI? ​Dean offered his perspective by stating that ‘engagement and AI may seem contradictory, but there's a clear benefit when HR uses AI to streamline admin tasks, freeing up time for vital human interaction. Tools like Koios, for instance, offer Acoustic AI, helping HR understand team and individual personalities better, for more tailored approaches. Professionals must approach AI implementation carefully, ensuring ethical use to maintain trust and transparency in the workplace.’ How can we make sure our services stay personalised while using AI? Dean responded, ‘By leveraging AI to handle time-consuming tasks. The best thing about AI is that you get to choose what it does and what it doesn’t. If you feel strongly about human interaction to enable personalisation, you don’t have to let go of that – just embrace AI to make those interactions better. Get it to strip data in the background for you, or to type up your notes and actions as you have the conversations. The possibilities are endless, and they can be tailored to your needs.’ Within your businesses, have you experienced any resistance to the adoption of AI? How have you handled these objections? Dean responded, ‘A lot of the resistance I have seen has either been a fear of trying or a fear of being caught. There seems to be a negative connotation with AI, that if you get it to do something for you, are you cheating? The answer is a resounding no, you are working with the tools available to make yourself more productive for your organisation. Robot proof recruiter, if you haven’t read it, you should. Especially if you are a recruiter or if recruitment is part of your job role. I’ll spare you the details, but it is an amazing read that showcases the fact you can never take the people part out of recruitment - you’ll always be able to provide a better level of service than a robot (at least for now) and you need to focus on the parts of the process where human interaction is at its most vital and automate/utilise AI to get back time in your day to improve that social element of the process.’ Do you feel Employee Resource Groups will be on the rise with the future generation of workers? ​Dean replied, ‘A truly hybrid workplace cannot function effectively without the right technology in place. That doesn’t even need to be AI. For employees to feel a sense of belonging in a workplace, there should be a seamless experience that goes beyond just having teams up on 1 laptop in a room full of 30 people. Again, this will only advance with time ... my eutopia is to have my whole team (who are based in the UK + Thailand) sat around a virtual desk, on a beach with an interactive whiteboard we can utilise in real time via virtual and augmented reality. You may laugh now, but in the next couple of years, VR and AR tech will be the staple of hybrid working and teams coming together around the globe. This doesn’t take away from the in-person experience and nor do I think it should. It should be a tool that compliments real-time working solutions.’ How can we support older generation employees in the changing landscape? ​Dean offered his perspective, ‘AI is truly remarkable. It embodies the futuristic vision many of us had as children—computers and programs taking on tasks for us. For those uneasy about it, I believe it's a matter of not fully comprehending it or lacking the skills to use it effectively. AI has quietly become a part of the workplace, and many are still navigating its intricacies. The focus should be on empowering employees to leverage AI to enhance productivity and value to the organisation. Those who resist or fail to adapt won't be replaced by AI but by individuals who embrace change and view AI as a tool for greater contribution.’ How can we safeguard against the risk of AI stifling creativity in the workplace? ​Lisa said, ‘I would say the opposite, if we use AI for the more regular and routine tasks then we will have more time to use to be creative! For example, instead of spending hours on creating a presentation for an important project - let AI do this creating for you and spend the time on how you want to engage with your audience instead. Using ChatGPT to find easy tasks that I would previously have spent a lot of time on has been a big change in how I work and allows me find space in the day.’ Is there a regional divide across different parts of the world? Are Europeans more prone to appreciate safety/job security than Americans? Lisa commented, ‘My thoughts are that globally we have been through a lot in recent years, covid affected everyone regardless of location. After that, we had war in Europe for the first time in many years which had major effects on the economy, which I believe has made people appreciate job safety even more and value this in choosing their next employer. However, in some parts of Europe employees are still very protected by labour laws etc so I believe it is different from America where it is more common to have short notice period and less resistance from employers to terminate an employment.’ Expanding on the key themes discussed in our webinar, we're thrilled to introduce our Thrive Guide – a practical roadmap for building a thriving workplace. ​Within the Thrive Guide, discover actionable strategies to enhance employee engagement, foster diversity and inclusion, and implement flexible working models. 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