As I type this, I feel in a particularly reflective mood. I am sitting at a bar, in Palma de Mallorca, where I should probably be partying or eating chipirones (trust me, there will be lots of eating, but at most a geriatric amount of partying). As I sit here, I am extracting learnings from Q1, from 2022, and generally from the last few years of management both at Crowdcube and 3 years in management at tastePal. So this is really 4.5 years of reflections. Leadership is a fascinating thing. Intangible. No right or wrong. 50-50 moments. Off-the-cuff decisions.
This post will primarily focus on 18 months as Head of Sales at Crowdcube. Grab an avocado, dig in, and let me know which parts you disagree with.
Also - disclaimer is that there may be some glorious full sentences, and other points that feel like messy bullet points and should have remained jumbled scrawls in my mind. Such is life.
Disclaimer 2.0 is that if you're not currently in sales or management, you might find this to be an extremely dry read. Don't say I didn't warn you.
Here’s 26 reflections and learnings. Bon appetite.
(I reserve the right to completely change my mind on all of this by this time next week).
1. Remuneration
Incentivize on upside. Sales people will always want more money. They are hungry, motivated, driven, smart people. Where is the upside to working on Saturdays and Sundays outbounding to be the best in the team if commission is capped at a level disproportionate to time invested? This is how sales people think. These are highly intelligent people with opportunity cost in their lives, so committing time outside work hours needs to feel worth it. The upside needs to feel potentially life-changing. A sales-person wants to buy into what they’re selling, as if it’s their own business. And they want to believe - they need to believe - that committing their blood, sweat and tears can lead to outsized returns. Ofcourse this commission needs to be proportional to revenue brought in by the individual, and needs to be carefully considered on a team relative to individual level. Would outsized individual commission lead to a disruption in culture of "stealing" leads from other team members? Is hybrid model of team and individual commission preferable? Details depend on structure of team and company revenue, but the principle of outsized (potentially life-changing) commission potential needs to apply to get the best, most motivated BDs.
2. Lead by example
A Sales Manager or Head of Sales needs to gain trust and respect early on in the role. Key way to do this is to lead by example by being exceptional at sales, closing deals that are seen as “marquee”, and being the model to aspire to. One of my failings was that when I started the role, I became so transfixed on the “management” side of it, and I wanted to allocate my pipeline to the new team members to boost their pipeline - but it came at the cost of bringing in deals myself. I became rusty, I became more of a manager than a leader or a world class sales-person, and I jeopardized the respect of the team as my role appeared more administrative than operational.
3. To consider when rebuilding a team
Hire fast - if hiring is priority. It is priority. Easy to do 11 things at 50% quality, but then hiring can take months. When there are key hires to be made, I recommend throwing everything at it.
Based on recent learnings, I recommend going this route if you need to make a great hire quickly - Do all of these in conjunction with each other, simultaneously: Use multiple recruiters; Otta; Flexa; Update your Linkedin page as “Hiring”; Post about it; Outbound top candidates yourself; Get different teams in the company to share; Offer referral incentives within teams; Revisit salary band and commission if needed. Do whatever it takes to get a high volume of top candidates as quickly as possible, because for any business where sales cycles take months, taking months to hire new team members on top of that in a rebuild is suicide.
4. Learnings from Interview process
There is no perfect process. I have learnt that a task that is representative of the daily job is helpful - for the individual to present in an interview and to talk through their thinking. Look out for soft skills - the little things like if they pause after making their point to see if you have questions or feedback, look out for if they are confident enough to provide substantiation to what they have stated in the task. Challenge them to see how they hold up to it. Disagree with them. Challenging and disagreeing will test how, even under pressure, they are able to show confidence and control the room - because clients will challenge them and disagree with them so you need to test it here first.
Be sure to give them enough time to discuss their questions with you, and be generous with your time - giving a clear view of the business’s growth plans and commercial model so they have as much information as possible to make an informed decision if they want to proceed. Remember - interviews should be a perfect fit for both, not just the employer. Final point on this - If the candidate is a 7/10, it’s a “no”.
5. If the majority of your team members are new
Pour your heart and soul into training them to be the best. If there are multiple people being onboarded at the same time, they are the future of the team - and your investment in them now may only yield rewards in a few months time, but those rewards will be worth it. Do not overlook the importance of an excellent onboarding
6. Onboard plan learnings
Be conscious of “nice to haves” versus essentials. “Nice to haves” may extend onboarding plans by weeks, but that theoretical training may only come up with clients 5% of the time. Think about onboarding in terms of the 80-20 rule. Get candidates to know enough to start working with clients asap, and optimize for practical learnings “just in time” rather than “just in case”. Get them in front of clients early, join them on meetings, and do full debriefs with them on what they did well, and what they can improve.
Aim for quick wins with clients - if you have a strong inbound and partnerships channel, be sure to give straightforward deals to new members of the team to boost their confidence and to demonstrate to them that the onboarding has been effective, and they know more than they think. I am a big advocate of the idea of learn-by-doing more than overwhelming with theory which has no context in real client situations. I remember when I started at Crowdcube, I felt overwhelmed by the theory. The onboarding was 4-5 weeks of theory but I didn’t have much of a reference point. Then when I started with clients, it felt almost like I was starting from the beginning because I wasn’t fully absorbing the theory at the time (maybe that just means I’m a slow learner). The goal now is that our Business Development Managers can lead meetings by the end of week 2. Get quick wins and iterate their learning. One of the big breakthroughs in our onboarding has been the use of Jiminny (you may know of their competitor, Gong). Being able to watch / listen to other team members’ historical meetings is a game-changer. Ambitious BDs take it home, drink in the content on weekends, and arrive at work in week 2 as if they’re 6 months in because of the quality learnings available.
7. Introduce new hires into the culture early on
It’s extremely important to make new hires feel at home as early as possible. Put yourself in their shoes - new company, new role, new people, significant pressure, and some have even moved cities or countries. We need to do everything we can to integrate them seamlessly. I strongly encourage having sessions already booked in their calendar and their systems ready for setup. I’d advise also having a team lunch on their first day or first week, and/or a team or company social to integrate them outside of work hours. Details matter for new hires.
I joined Crowdcube from South Africa in 2019. I arrived in UK on the Friday and I started work on the Monday. We went for team lunch on my first day and there was a social that week - it made all the difference to me in feeling “like home”.
8. Training never stops - and has to be consistent
Have recurring training sessions in the calendar - some weekly/ some monthly/ some quarterly.. Have a clear map of what training is needed when (it can be a mix of Objection Handling, Compliance sessions, Value Proposition Refreshers, Marketing Refreshers, Peer-to-Peer coaching sessions etc). Be on top of where the team’s weaknesses are and constantly be looking to fill those gaps. Send quarterly Google Form out to the team to check in where their training gaps are - for them to as honestly as possible state where they are unsure, so that you can be proactive in booking in necessary trainings.
Host a weekly meeting for the nuclear team - this should be a small session that’s as interactive as possible - each individual in the team should discuss what are priorities for the week; how can we help each other; what did we learn that week; current quantitative position in the quarter. The goal of that weekly session should be to create a culture of supporting each other, and sharing mistakes and learnings for accelerated team learning - there is no room for ego.
One of my mistakes has been to only set up Weekly sessions like this very late into my role. This meant for the last 18 months, some team challenges either only came up in discussions in the other training sessions, or I needed to pick up trends in our one-to-ones. That leads to higher likelihood of reactiveness. The Weekly sessions provide structure, support and accountability and if I could start again, I would implement that Week 1 as a no-brainer.
9. Professional Development is key
Once a quarter, run Professional Development plan sessions with each individual in the team. The goal of this should be to work on what they want to Stop, Start and Continue in their current role, what their medium term goals are in the company, and what their medium / long term goals are in their career. These sessions are key to show you care - and that you are going to work with them to achieve their goals.
Consistency is key - one of my mistakes has been that I started with these plans, but then as things got busier, I relegated them and haven’t done them for the last few quarters.
10. Never get complacent on the team’s ambitions
Tying into the above point; be proactive in understanding each individual’s professional ambitions and do everything to clear the way for them. Fight for them for salary. Give clear quantitative goals for them to strive towards and stick to your word if they achieve. Fight for gender equality on pay. They need to feel that their boss wants them to grow and succeed. That’s the only way they will truly give their all.
These are critical factors in morale and indirectly on performance. I have sometimes done this well and sometimes not - it’s something I will always strive to improve on because I know it’s so important for me if roles are reversed.
11. Be a data machine
Have a rock solid definition of what good looks like in terms of handover volume, estimated revenue, closed lost rate, outbounds-to-meeting-to-deals-signed ratio. It’s extremely difficult for a new member of the team to come in and know "good" if numbers are murky. I haven’t been excellent at this - I’ve had a good grasp of the big picture numbers, but haven’t been as laser focused on the micro numbers as I should be - another big learning.
12. Be physically present
As a sales leader, you should be available wherever the majority of the team is. If the team is in the office, you should be in the office. Being physically present allows for serendipitous moments after a client meeting where you can provide advice and support - it’s really difficult to quantify the value of that, but I believe it’s extremely high. It took me a while in the beginning to adapt to this - I was so pro-remote work that even when the majority of the team were in the office, I was working from cafes and from home. Oh I just love working from cafes - too much. Over the last 5 months I’ve worked most days in the office when my team has been there, and I’ve seen the serendipity in action where perhaps previously they wouldn’t have sent that additional Slack message asking for support. Little things like this can make a big difference.
13. Find a working model that works for the team
Whether it Hybrid or flex or remote, the manager needs to understand each individual in their team. Where do they live, what works best for them, how productive are they in the current system, what is the composition of their average day. The manager should have that discussion with each individual. This decision should not be top-down enforcement. I believe the hybrid vs. office vs. remote is one of the great professional challenges of our times - but I also believe it’s really simple. We should trust each other. We should show each other respect, find a way that works for everyone, and if we do that, the team will feel it and want to perform at their best.
14. Morale is incredibly... incredibly important
Tough times in a company may lead to cost cutting. It may lead to a lack of salary increases or bonuses. Sacrifices need to be made. But morale will always be important. No matter what. The manager needs to understand how to boost morale of the team - and it doesn't need to involve significant costs. Senior leadership should support this. It may be simple things like celebrating birthdays of people in the team, vouchers as a “congratulations” for successful deals closed, or a proverbial arm around the shoulder of support . Little things, but if done proactively they can show the team that the company has best intentions, and backs the team to turn things around.
15. When someone in the team is over-performing, show recognition
Sales cycles take long and sales may not convert into revenue immediately (at Crowdcube it takes 3-4 months after signing a deal for it to convert into revenue). A BD needs to know they're doing a good job. If you "lose" 1 deal after winning 9, it can still feel like the world has fallen apart. I recommend asking other senior people in the team to send a message to the achieving team member or take them out for coffee/lunch - it’s a very simple low hanging fruit way to show that the person is recognised and appreciated in the organization
16. Continue to sell at a high level
To re-iterate this one. The manager needs to continue to sell at a high level. How can you train / lead / be proactive on what's not working with Product Market Fit if you’re not staying sharp? Such a big part of the job of a Sales Manager or Head of Sales is objection handling and help with getting deals over the line, and it really is like a muscle that needs to be exercised to experience hypertrophy, or else it will atrophy. Volume may be lower, but value would be higher. Close high value deals, and host “learning sessions” on what you did to close those deals. The learnings and trainings never stop
17. Join the team on their sell and encourage team-sell where necessary
Self-explanatory. If a client brings multiple stakeholders onto a meeting, we should do the same. If the deal is high value, we need to recognize that by bringing in people who have the gravitas of experience. The subtle signaling of team-selling shows that you value their business. This is massively important not only in a competitive environment, but generally if you want to be the best consistently.
18. Be an ultra-effective liaison with other key teams
Be proactive on engaging with marketing on assets that are needed to help with the position of the value proposition. Get very close with the campaign / account management team - because they have the best understanding of if client’s expectations have been managed appropriately by the sales team. We need to constantly get feedback from them and improve.
19. Competition.. Oooh Competition
Use competition as inspiration to be better. Show them respect. They are clearly not sh*t at everything, and clients know that. Acknowledge to yourselves internally, and directly to clients where your competitors are strong, and give clear and practical thinking on why you have chosen to do it the way you do it. There is a reason for every decision in your business, and your sales team should buy into it with every fibre in their being and be able to explain the rationale to clients like their life depends on it. Use competitors as fuel to be better, rather than bashing them. Hold objection handling frequently to keep the team sharp
20. Firing
Do it the right way. When concerns start to arise, initiate a firm Performance plan with assistance from HR. Communicate up front that there is job risk, and provide clear areas that are not where they need to be (this again highlights the value of having a good understanding of the quantitative "what good looks like" in the role to use as a benchmark). Share written performance plan and work through it together candidly and transparently with the goal of turning it around and turning the individual into a top performer. Do not just one day set up a meeting and pull the trigger. It’s not fair to the individual, and doesn't give them a fair chance to turn it around - and the knock-on effect on team morale is profound. Probation is different if a wrong hire is simply wrong hire. But after several months / years into the role, there is a certain level of respect and share of responsibility that is deserved. I had big learnings on this one, and definitely feel that I’m much better prepared now to handle this situation in future.
21. Resignations
It is your goal to see it coming. A surprise resignation is a failing of management, because the manager should have their finger on the pulse of the team at all times. If there is a risk of resignation/s coming, start the hiring process early. Hiring can take longer than hoped because, as Liverpool FC manager (I had to get them in here) Jürgen Klopp says "it’s better to have a hole than asshole". Never rush hiring. But if you know in advance you may have to hire, it makes that much easier.
Support the resignation of the employee and do whatever you can to help them. If you have helped them to take an exciting step in their career that is a better fit for them, you have succeeded as a leader, and that’s what it’s about.
22. Misconduct
If there is anything that looks like it even has the slightest chance of misconduct, escalate it internally to those who have had experience dealing with previously. At a company party social, a leader still has to take responsibility if you see something that doesn't look right and needs to act swiftly. Then escalate as if it's the most serious version of events, rather than seeking to handle it yourself.
23. Process and operational improvement
While juggling the above plates, the manager’s finger needs to be on the pulse of where major blockers are in the team. You need to use any goodwill internally to push for this and put together a strong case for how that efficiency increase can translate into results. A real life example (and another mistake I’ve made) at Crowdcube is that Inbound applications from clients could be much slicker and more efficient. I noticed this and had it requested many times by people in our team, but I de-prioritized. If I had sorted this out upon first request, we would have had a more efficient inbound system over the last year, and it’s difficult to quantify how many hours could have been saved for clients and for our team.
24. Clear blockers for the team to excel
It could be an escalation of a deal that has become extremely complex, or it could be frustrating admin that’s stopping them from doing what they do best. A manager needs to remove blockers. If it’s a complex deal that has stumped the member of the team - it’s the manager’s job to jump on it , level with the client , sort it out, reflect on learnings as a team and move on, rather than letting the complexity fester and disrupt that BDs pipeline and time for hours/days/weeks to come.
25. Be ruthless in prioritization
Between hiring, onboarding, training, one-to-ones with team, one-to-ones with individuals in other teams, professional development, outbounding, closing deals, building strong relationships with adjacent teams and striving for greater operational efficiency, it's impossible to do all of them at 10/10 all the time. A sales leader needs to be able to say no. I recommend setting 3 key priorities on any given day, week and month. It’s such a simple concept - but I remember from his book, Bob Iger advocated for this when he became Disney CEO when he took over a mess and had to describe his objectives to the board - it worked out pretty well for him to provide that much needed clarity and focus.
26. Manage upwards
Be open to take coaching and advice from your boss and boss’s boss. Be a company-person first and strive to fulfill the desires of your manager. But hold convictions, be candid in discussions giving the thoughts and experiences of what you believe is right based on being in the thick of things on a daily basis, and have evidence ready to support your case if disagreeing with your manager. Be proactive in seeking advice from senior leadership in the company if it feels like the team is facing a significant and concerning challenge. Be persistent in ensuring that the challenge is taken seriously even if that means discussing with multiple stakeholders in the business.
If you have enough conviction in it, you have to fight for it.
So those are my reflections.
I will have many more over the next 18 months, but I felt the need to get them down on digital paper. I realize about myself I often need 2 or more attempts to get something right, but the beauty of the last 18 months is that I have been exposed to a little bit of everything and often more than once, so my skills have had many opportunities to sharpen and re-sharpen. I haven't always prioritized effectively, and I’ve often fallen into trap of being reactive. Every day in Sales Management there are new challenges and new opportunities to improve. That's the beauty of it. Makes it fun. I hope at least one of these thoughts are interesting / useful - and if not, it was cathartic for me to write down - so we all win.
Onwards and upwards!
