Why you’ll want to read this article before joining a startup as employee 1–10

Deepika Singh
May 5, 2018 · 18 min read
This image relates to Alore in no way and yet in some way. Steep uphill climb to gorgeous views !

An honest account of what it is to work at a pre-revenue stage, bootstrapped tech startup as Employee no 8 !! and what startup life teaches you for real

“You’re in for a career suicide! why the hell do you want to work for a startup when there are so many multinationals across the globe !! ??!”

That’s the first thing I got to hear from my family when I decided to take up a senior alum’s offer to just “explore” a role at his company.

As if convincing the family wasn’t enough, some friends from B-School jumped in saying “you’ve got to be crazy to get into a bootstrapped(non-funded), pre-revenue startup!! “

Well I guess I was, or rather still am 😊 but hey, I love what I do!

Of course, I understand that entering a Bootstrapped startup is like jumping into the sea with your feet tied. You either sink or you learn to swish like a mermaid and explore the ocean. The deal is to learn to survive really-really quick!! Tick-tock, tick-tock !

Oops haven’t introduced myself yet. sorry!

Hey, I’m Deepika!

Head marketing at Alore, Mother of twin toddlers and love my M&Ms — Marketing and Mountains !

My startup story

Mid 2017, as an alumni chapter president I reached out to Vikas Jha (VJ) -a senior alum from B-school about a get-together we were planning. Mid conversation he just randomly asked ” why don’t you explore joining my venture”. I thought he was kidding because we hardly knew each other and swept the thought aside until he asked me again some days later. I had a call with him to just respectfully listen to whatever he was saying (half intending to say no), but loved the idea of Alore so much that I decided to explore further with a meeting with him at Bangalore. Also, I must honestly admit I was thinking of look for a new job because I wasn’t happy in the previous one. It all seemed to work for me at that point. Serendipity of sorts.

I flew to Bangalore to understand things in detail and do a founders audit. Basically, understand what Alore was at that point, what VJ did, company culture, colleagues etc and see if I gelled well with the team.

First day of meeting, VJ asked me to tell him what I’d like to work on. I pitched some ideas that I felt were relevant to his business. One of them was to have a thought leadership publication. anddddd

Day 2, he sent me solo, to interview a reputed CEO and Startup mentor with decades of experience.

Day 3, I was writing out emails to scores of CEOs and VCs to check if they would be available.

As an extrovert and an experienced professional, I wasn’t rattled or hazed but rather amazed at the pace of how fast things went from idea to execution.

That’s continued ever since.

Our mutual audit ended, with him saying this to me before I left — “I’m creating the product, you tell me what you can do to get it out there in front of a million people” — Nothing before and nothing after.

The Startup life

Well I agreed to join Team Alore as the Head of Inbound Marketing and employee no 8, I was the first senior role hire.

Contrary to what Hollywood would have you believe, Startup life is not beer-pong tables and paint ball sessions at work. Yes, there’s music, pizza, Friday drinks and people in shorts sitting on bean bags all around you but there’s also crazy levels of energy and focus that you can sense the moment you step into our office.

The Alore office

At the time of my joining in August 2017, the product wasn’t ready yet, there weren’t many processes in place, not much clarity on what my tasks were, No KRAs defined (in fact I was asked to choose my tasks and KRAs), the team wasn’t totally in place yet but everyone working super-focused inhuman hours six-seven days a week.

Besides VJ-the CEO and Founder, we had 5 developers, a marketing manager and a business development manager dedicated to Alore. Within a month I brought in a team of 6 freelance content writers who reported to me. Things were moving real fast and it was a happy high.

I took three weeks to make an initial detailed marketing strategy which looked like this:

Snapshot of my first marketing plan for Alore

I remember when I presented it to the management, one of the senior advisor’s from South Africa remarked — “This looks ambitious, I’m curious to see how much of it we can really do”. I remember thinking in my head “Oh c’mon, all of this !!” — I had to learn a lesson on that one and how !

The Startup roller-coaster unleashed:

Alore CRM was my first stint at a technology startup and I swear to God no MBA class could have prepared me for the wild ride I had in the initial days.

In a startup, as a senior employee you’re at a position when you need to fail fast and learn faster. You’re unlearning and re-learning like never before. It sounds so easy to preach this but trust me, you learn the hard way. The darn human instinct to seek the easier path often gets you to take crappy decisions.

There’s also this aspect of taking salary cuts. You’d be surprised that I’m back to earning what I earned in 2013 (which is a bummer) yet I’m intrinsically motivated to work double of what I have ever worked before. Of course, I have ESOP and all that but that’s something for later. You wonder why I took this cut and I’d say it’s the tremendous job satisfaction of giving form, direction and shape to your ideas.

The initial days at Alore were plain crazy. I was working crazy hours and donning many hats — Recruiting and on-boarding content writers, Planning, Executing, Analysing data etc. It was a dizzying pace of work until the cracks began to appear. The marketing manager we had earlier hired, resigned along with the Business development manager. While we actively began searching for replacements, we had to take on additional responsibilities.

I shortlisted two candidates and went in for the one I had a gut feel about showing more promise. He left after a month. I remember feeling bummed about it for a few days. I couldn’t figure out what irked me more — the fact that my gut feel went wrong or I didn’t see it coming. I learnt quick and am super careful about hiring now.

Startup life is low on processes. This is a no-brainer and I kind of knew that. To his credit VJ had been taking many measures to document each process we made but strategies and life was so sonic that it was difficult to define processes for every single aspect. In fact, we used the lack of it to our advantage as much as we could. In this same regard I saw a difference in workstyles as well.

While VJ is extremely process and data oriented, I’m a bit low on that and go in creative flows which somehow works great for us owing to the need of our respective functions. However, we both understand that as I lead a function, I need to have my feet in data while I take creative flights in my head. When I hire my team members I “need” to have them process oriented to be able to execute sharper and better.

We sat and discussed in detail on what marketing would mean for us- Being memorable, being personal and talking like we were talking to a friend at a favourite cafe ! We wouldn’t ship fluff and always seek and talk knowledge not information. Anything else would be failure.

Working at a startup demands insane work hours. I work an average of 70–80 hours a week. In my case it’s not easy to manage that from office with me being a military spouse and mother of twin toddlers. Working the crazy hours of work a startup led me to seek a remote working option. So I work from office for a week and then I’m off to wherever I can manage my family life better with a solid support system. I’m able to manage my life this way and it’s important for startup employees to be able to find the balance and excitement.

I totally agree with Daniel Gulati, co-author of Passion & Purpose. “Startups are cauldrons of energy, stress, and joy. You need to be fundamentally excited about working there”

Here’s some learning I’d want to share with anyone who is looking to joining a startup as employee 1–10

1. Do a founder’s audit

Yes, you read that right. Before you join a company as employee 1–10, you should ideally spend some time to get to know the founding team and assess pragmatically if you’re a good fit and gel well. You need to get a trailer of the life at the startup to see if you feel “great” there. (feeling good won’t last you more than a few weeks!)

2. The Salary Package

So you don’t have to go work for free. Financial worries are a huge factor for balancing personal and professional life. It’s simple, if you’re working for free then you’re a co-founder and take equity accordingly for it.

If you’re joining as an employee go in for a package that takes care of your pressing financial needs and have a performance based variable component to your salary. In addition to this you can check for ESOP as an early employee which shouldn’t be considered part of your package but a lottery. If the company makes money some day you make cash else its just a lottery ticket in your hand.

3. Have company Goals and personal goals and align those

This goes specially for those of you looking to join as senior hires. Have a clear understanding of the company’s goal and align your function’s goals to it. Form sub-goals. Now, (and its important) figure out what do you want to personally gain from this and learn. Identify three personal goals out of each company goal. e.g. if your company goal is to generate leads from Lead magnets, your personal goal should be to know how to create a lead-magnet from scratch, know what tools are used, internalise how these programs work.

4. Jack of all trades master of most

Startup life demands expansive knowledge which isn’t thinly spread. While at a conglomerate you can specialise into social media or community management, in a startup you really must do many roles and be really-really good at it in a short time frame. As the head of marketing I am writing content, I’m a community manager, editor, social media manager, digital marketer, brand management, Internal and external communications, PR Manager and what not. I’m thin in some buckets but good with most and plan to better myself with learning goals.

5. Productivity is first a state of mind and then practice

Startup life demands you to not just be efficient but productive. It’s just simple, you’re efficient when you can finish ten hours work in seven and call it a day. You’re productive if you can finish ten hours work in seven and utilise the “free” three into finishing tomorrow’s tasks today.

6. Compartmentalise and Prioritise

It helps to divide your long-term goals into short one-month batches. Some argue it should be as early as two weeks, but I have found that a reasonable time to see results coming out from projects is about 30 days. e.g. a piece of content that you wrote or reach-outs that you made.

Also, the first six months should go into understanding the startup’s ecosystem and knowing every detail. You should be so clear with it that you could even handle support for a week or two if needed.

The next six months should go into solidifying your pillar in the startup — what is it that you bring to the table and can leverage.

Have your priority list made every week. Decide what it is that you want to achieve for the week and focus with full gusto on that. You might fumble a few times but will soon gain a knack of it with the million things on your plate and finite time to execute.

7. Adopt the company culture or create one quick

With no company culture in place there is chaos, slowdown, attrition and stress. The only way to ensure this is by deciding what really you want to gain from it all. Let me get this straight — culture starts from the top and I was lucky enough that my boss had already defined the culture framework for us early on based on his expectations and previous VC and entrepreneurial experience.

I found adjusting into the Alore culture easy because I felt one with it, many who didn’t, left within weeks or months of joining because they weren’t aligned with the goals, mission and methods at Alore.

“Founders who rate the importance of culture lower than a 10 on a 10-point scale are 70% more likely to have higher employee turnover rates compared to founders that rank the importance of culture a 10”. (HBR)

8. Delegate wisely

It’s important to delegate your tasks and know what’s up your alley and what not. You can’t be swimming in the weed if you want to swim in the ocean. e.g. I have a freelance panel of content writers who help me with the content but when it comes to writing thought leadership stuff I find it easier to do it myself. However, when it comes to writing a listicle or how to article I delegate it to the CWs.

9. Cut loose dead-weight

Heartless as it may sound, team members and colleagues who do not add considerable value but rather constantly increase the distraction from work are dead-weight to the organisation.

This was a hard learning for me because I tend to relate well with people and empathise. However, it took me a few months to understand and strengthen my mind to the fact that certain hires are not just aligned with your company culture, vision, direction and pace. It’s not that they are bad employees, it’s only that there are diverging needs from the relationship.

I say this with experience and learning — Lean is mean sometimes!

10. Establish scalable processes

This is something that will come over weeks and months. If you can, then always try to form a process with minimum bottlenecks and in a way that even twenty more people joining tomorrow can follow the process with ease. A scalable process saves tremendous time in a young business specially when the product goes live and you constantly feel out-gunned and out-manned.

11. Plan. Plan. Plan.

Okay this is something we all know we should do and yet end up not doing. Plan at three levels

a) Plan your month

b) Plan your week &

c) Plan your next day — every evening before you close for the day, plan your next day in your organiser/diary or wherever it is you find convenient.

Well planned is half done and it’s sooooooooooooooooooo true.

12. Take in your thinking twenty

Spend twenty minutes a day at work to just “NOT” do anything and not talk to anybody. No screen time either. These twenty minutes are yours. Think about whatever it is that you want- work, personal or space mysteries. It’s just a super effective trick to give your mind a break and refreshes you. I have often found myself solving problems and getting my best ideas after these twenty-minute breaks.

13. Socialise

Okay Introverts might still find this aspect passable but extroverts like me derive energy from people. In a small startup the number of colleagues is small as well. It’s almost a drawback when you want to just bounce your ideas with colleagues to gain insights from collective experience and lack it. Here’s when what you lack within your startup, you need to seek outside — professional advice from people in similar positions. Be part of groups, communities, events etc where you can meet like minded people and network professionally.

14. Bond with your colleagues

To be really able to handle the stress of startup life you need to find things in common with your colleagues and more so with the boss. It’s essential to have a founder who isn’t just a boss but somebody you can go to with your personal issues as well. e.g. I’d known my current Boss VJ for years now but only as an acquaintance. It wasn’t until we decided to work together that we really got to know each other. The bridge that you build helps you tide over the rough days when the boss isn’t in a great mood or when you’re going through a tough day.

Once, my kids were unwell while I was working remote from the Himalayas and had a pressing deadline to meet. The boss sent Pizzas to cheer up the kids. Stuff like this makes it easier to be giving your best when you know you have work taking care of family.

Also, with colleagues you know well, there’s understanding and alignment for the bigger goal at work and you tend to not fret to much on trivial issues. You form a formidable team if you have a wavelength match. I like to imagine myself and my boss as the Sheryl Sandberg to M Zuck only that I’m younger than my boss. ( ha ha I just had to say that in case the old man is reading this 😉 )

15. Focus on Sales Enablement earliest you can

Okay this one goes for sales and marketing professionals. Companies whose sales and marketing teams work together see 36% higher customer retention and 38% higher sales win rates (Hubspot). Greater communication between sales and marketing employees helps plug in gaps and expedites creation of collateral when you’re discussing what you’re planning and up to that week over a coffee or lunch.

Being a highly fluid environment sometimes early-employees need to function as an extended brain to the founder. I struggled with keeping pace many times and understanding an off-hand comment meant a change of strategy from that very day on. Now I’m more alert about conversations and cues.

16. Don’t just work, go an extra mile

It’s great to work and deliver what your business promise. However, its super important to focus on something additional that helps you connect with a bigger network and meet new people. It of course helps in building a brand which is an unbeatable asset to have. For e.g., we have started building our Facebook community on sales and growth hacks for small businesses. Our aim is to sell nothing to the audience but to just engage with them in conversations — share ideas, get advice and plain networking.

17. Be yourself

Authenticity trumps “Polished Executives “. The time and tide of having bashful hustlers in suits screaming out their practiced pitches is long gone. In the digital today we humans crave and value authenticity. Write like you think, Speak what’s on your mind. Of course, be respectful all through but don’t ever fake it!

18. Always be Hiring

I recently read an HBR article which stated that when you’re in a startup, the first ten people will determine whether the company succeeds or not because you need the A players the most. The theory of it we knew, but we learnt this through experience

Over time when you repetitively get burnt with hiring the wrong candidates, you will figure out what works and what doesn’t. Interviewing and spotting the right candidate is an art and I have so much more respect for people in HR now. At one point of time we had scaled up to a team of 16 employees at Alore thinking that the more people we have the faster we would scale. We were so wrong.

It eventually merges into the question of dead-weight. Many of our hires were smart people looking for 9 to 5 jobs and weekends off. I am certain they would do extremely well in bigger corporations but unfortunately that’s not at all what the startup life can offer. Sadly, we saw them leave one after the other. It also taught us lessons on what we must not be doing while hiring. Funnily enough we are now a team of 7 people today and managing the same work and putting in similar hours.

18. Let Talent be the only thing that matters

Sometimes the smartest people for your job don’t live in your city and probably don’t want to. You have to take a call on does it really matter to you to have the person sitting right in front. Thankfully I have a team that understand the fact that Talent trumps location. I am perfectly given the choice to work from any place in the world as long as I have good internet and my deadlines are met. Will talk about my flexible remote working life some other day!

19. Be consistently and constantly transparent

Startup life requires transparency. Everybody understands the highs and lows, the jubilation and frustration that comes in the startup life. It’s just the way it is and its almost a right of passage for every startup employee. Being secretive and hiding your lows wont ever help. When you need help, just ask. eg I recently faced burnout and was having trouble keeping up with the pace. I openly discussed with the team and they understood and gave me some time off to just relax and spend time with family and friends. Result — I came back super charged within a week.

20. Have the confidence to hire people better than you

This probably is a major one for me personally. In a startup you start with a role but soon realise you don’t know everything you should to succeed the best and fastest you can. You learn things quick but sometimes its not enough or rather doesn’t make up for the presence of Subject-matter experts (SMEs). You understand quick that if you want the business to succeed you need to access people smarter than you and convince them to join you if they can.

21. Understand the difference between Tacit knowledge and explicit and use them well.

As an early employee you will see the company through many phases. It’s the most exponential period of the learning phase until the scaling phase kicks in. Tacit knowledge is what comes through experience, exposure, learning and counts for your “I just know this will work” decisions. Explicit knowledge is the transferable documented knowledge you can disseminate across all new hires from day 1. In a startup when the number of decisions you make in a day are many and hold weight, you need to evaluate constantly on what you’re doing and how each decision fares based on your tacit and explicit knowledge.

22. Become an expert in evaluating Resources vs Relevance

As a startup you will find yourself constrained for resources. Utilizing finite resources for maximum gains becomes a habit for a long time to come. You begin to evaluate initiatives based on what really would work for you. e.g. in my past life I’ve been a jet setting consultant charging by the hour. Right now I have to pragmatically evaluate if I want to go attend ten conferences or two.

23. Meritocracy is key — You care about peers more than perks

The startup life teaches you this trait so well that you feel it in your bones. It’s all about what value you bring in, how you appreciate and support each other and how the smartest ideas get implemented. It’s really not about who the idea came from and it’s very liberating in a way. You’re always a team. You’re not thinking I gave ten idea this week, so I want a corner cubicle. No. You’re always thinking of company first, your peers second and yourself third. Perks don’t even feel like they’re there in the picture.

24. Be Intentional

You learn to be intentional about your every step. If you’re in, you’re wholeheartedly in, if you’re out you’re completely out. You can’t be partially involved in ideas. and this slowly transcends into personal lives as well. At least it did for me. When I’m with family on Sundays, I don’t even check my phone or emails.

25. The startup mindset

The real transformation is the mindset — You have direct access to the founders and investors as a senior early employee. You have the power to make decisions that get implemented in minutes and see results. You don’t brood and cry over failure but just quickly roll up sleeves and get onto Plan B in no time. Its just how it is.

26.You realise technology is a blessing.

With a hundred things to take care of and the minuscule resources and finite time, you slowly begin to adopt technology to aid things getting faster. e.g. I plan on Asana, If I want to find good keywords I go to SEMRush, I want to check plagiarism I go to QueText or Grammarly, If I want to see how I divide my day I use RescueTime to see what my productivity is. The point is to choose tech tools that work for you.


I’d like to say that enter the startup life with your eyes wide open and knowing what you want to achieve. Know your founder best and team next best. Have clarity on the company goals and then identify your personal goals within and align them well.

We are all clueless when we begin specially as employee 1–10. Don’t fret over it.

If someone says contrary they’re bluffing. However, take time to do a founder’s audit, know your team, know the broad expectation spectrum around you. Make sure your basic financial needs are being met fair and square because with that missing you’re going to be a grumpy impatient person on the team. Utilise this opportunity to be a creator of your trajectory and jump onto the fastest learning curve you can find yourself. Focus on the mindset and tacit knowledge and you wil find things falling into place within weeks.

As for me, I’m excited about the coming months and years. Literally!! The professional landscape is like an open canvas to paint and I’m in the Picasso creative space. Personally, my husband and I look forward to watching our kids start school and be around to see them grow as much as we can. Yes social life remains a slight challenge but right now the aim is to give 100% to what I have high on priority — Family and Alore. That’s the promise that’s the love 😊

Originally published at blog.alore.io on May 5, 2018.

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