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Working for Small Companies – Why & How Sabrina Castiglione Chief
of Staff
Why think about Start-ups? Things to consider when applying to Start-ups What you should do next!
CheckRecipient: Working for Small Companies – Why & How
WHY THINK ABOUT START-UPS?
A career in start-ups isn’t for everyone – but it might be perfect for you!
For the right person, small companies can provide a great and stimulating opportunity
Here are some factors to consider when thinking about whether a start-up might be the
right place for you!
CheckRecipient: Working for Small Companies – Why & How
WHY THINK ABOUT START-UPS?
I want…. More Impact
In smaller companies, the effect of your actions is much more visible. Everyone’s a big
fish in a small pond!
You get to grow something from the ground up!
There’s nowhere to hide!
At a large company, it’s usually an entire team working together that will influence success. In
start-ups, everyone's individual performance matters. That’s a lot of pressure!
The flip side… Pressure!
CheckRecipient: Working for Small Companies – Why & How
WHY THINK ABOUT START-UPS?
I want…. Variety
In smaller companies, with fewer people, people tend to get stuck in on a broader variety
of projects.
You won’t be pigeonholed into one activity, and so the work is less repetitive.
You won’t have a stable workload and things change on a frequent basis!
Scope-creep is common and you’ll often find yourself with a lot on your plate!
With such importance placed on every person, start-ups have to be quick to hire and fire.
The flip side… Less stability
CheckRecipient: Working for Small Companies – Why & How
WHY THINK ABOUT START-UPS?
I want…. to Learn and Advance - FAST!
Start-ups are focused on fast success and fast growth.
You’ll take on more than what you were hired on for, probably get to take on multiple
positions, and learn two to five times faster than in a corporate position.
With fewer people at a start-up, you’re more likely to be promoted if you're doing well
Established companies have more developed training programs and give you more ramp-up
time.
In a start-up, you’re in the deep end from day one… so sink or swim!
The flip side… You’re in the deep end!
CheckRecipient: Working for Small Companies – Why & How
WHY THINK ABOUT START-UPS?
I want…. More Autonomy!
Generally, there’s less formal structure and bureaucracy in a start-up; with fewer rules,
there is more room for creative and entrepreneurial types to express themselves.
You get to decide how to do your job!
Start-ups lack a structured environment and chaos can sometimes reign!
If you find clearly established processes and instructions to be an important comfort, the ‘it
doesn’t matter how, find a way to get it done’ attitude might not be for you.
The flip side… It can be chaotic!
CheckRecipient: Working for Small Companies – Why & How
WHY THINK ABOUT START-UPS?
I want…. Equity!
Start-ups give you a chance to own a piece of what you're working on… and if the
company successfully exits, you get to share in the reward.
If your start-up is one of the lucky ones – the pay-out can be massive in the end.
In the early stages, funds are often low, so established companies generally offer more
competitive salaries than early stage start-ups
Benefits can be limited until there are more employees, and more funding!
The flip side… But that doesn’t happen right away!
CheckRecipient: Working for Small Companies – Why & How
WHY THINK ABOUT START-UPS?
I want…. a Fast-Paced Environment!
In large companies, innovation can be slow and results gradual - fruition can take
months; In start-ups, results can be immediate and there’s a lot less red tape!
Start-ups are dynamic, fast-paced environments that value initiative. And the breadth of
work makes them great places to figure out what you excel at.
75% of start-ups fail, and there’s always the chance that your major project could be
circumvented by an unanticipated advance, competitor, or invention
Additionally, you need to think for yourself, self-teach, and upskill to keep up!
The flip side… There’s a risk to that speed!
CheckRecipient: Working for Small Companies – Why & How
WHY THINK ABOUT START-UPS?
I want…. to Believe in Something!
Start-ups are mission-driven, and the intense atmosphere can spawn great creativity,
innovation, and reward
Start-ups are filled with go-getters and people who are willing to go the extra mile
With a required level of dedication from everyone that’s rare at a big business, emotions can
run high, hours can be long, and work loads can be significant.
Start-ups have a small workforce with huge missions, passion about seeing a project through,
and every person factors into its success: so it’s not as easy to check out for a while or coast.
The flip side… You’re all-in!
CheckRecipient: Working for Small Companies – Why & How
WHY THINK ABOUT START-UPS?
I want…. a Great Culture!
Start-ups are fun! Many founders come from stuffy corporate backgrounds and seek to do things
differently; a lot of effort is made for teams and workplaces to be social, collegiate, and encouraging.
Get a lot of smart, driven people together, and sharing the ups and downs of building a company can
be the most fantastic, rewarding experience, and here you can make friends for life!
The mission-driven atmosphere also brings people together; If you want to be a part of something,
and work with great people, on a great journey with a shared sense of purpose, this is the place to be!
CheckRecipient: Working for Small Companies – Why & How
ESTABLISHED COMPANIES OR START-UPS?
Who are we? What do we do?
Why – and how! -
you should get to
know us!
Established Companies Start-Ups
Pros Cons Pros Cons
More people around you in similar roles
to lean on & learn from
Impact can be hard to gauge Instant Impact Nowhere to hide
Well-defined responsibilities
Pigeonholed
Repetitive
Varied
Broader range of activities
Less predictable
Scope-creep
Less predictable
Developed training and processes Slower career progression Learn a lot and progress – and fast! In the deep end
Structured environment Bureaucratic
More autonomy
Freedom to define processes
Chaotic!
Salaries and benefits can be more
competitive
No ownership in the Company Equity Shoestring budgets!
Stable Slow to innovate Fast paced and quick to innovate Riskier!
9-to-5
Can sometimes be ‘just a job’
9-to-5
Can sometimes be ‘just a job’
Mission driven
A lot of personal responsibility
Hard work, long hours
A lot of personal responsibility
Brand-names and recognition Formal feel (although some people prefer
this)
Great-Culture You work for who?
CheckRecipient: Working for Small Companies – Why & How
NEXT STEPS
Who are we? What do we do?
Why – and how! -
you should get to
know us!
Pre application:
• Think about what stage of start-up you want to join (1-10 employees? 10-50?) and what kind of
model they follow (VC-backed means fast growth and high targets, privately owned are more
likely to aim for early profitability and grow slower)
• Do your due diligence! Not all start-ups are created equal!
• Does the funding come from reputable sources?
• What’s the business model?
• Who are the competitors?
• How is the start-up going to adapt and keep innovating to stay ahead?
When applying:
• A short but highly relevant and customised cover letter is always preferable to a long but clearly
generic one!
• Work out the relevant person’s (e.g. CTO) email address and apply directly if you can!
• Look at start-up specific job boards and attend start-up specific events & meetups
CheckRecipient: Working for Small Companies – Why & How
NEXT STEPS
Who are we?
Interview stage:
• Desirable traits to demonstrate (have your competency answers ready!):
• Culture is very important;
• Show them how you’re a team player!
• Demonstrate your individuality and interests!
• Demonstrate your adaptability, willingness to learn, and ability to self-teach and multitask!
• Show lots of enthusiasm! And be ready to explain why you’re enthused by the opportunity
and the mission.
• Make it clear that you are willing and able to go the extra mile, and do whatever is needed
to get the job done
• Show them that you know what you’re getting into, that you have considered the risks and
are coming to the opportunity with your eyes open.
• Learn the Lingo & about types of funding (e.g. VC-backed) and show that you understand
the journey the company is on!
Why – and how! -
you should get to
know us!
CheckRecipient: Working for CheckRecipient
Find out more!
Sabrina Castiglione
Chief of Staff
CheckRecipient
sabrina@checkrecipient.com
www.checkrecipient.com
checkrecipient.workable.com
checkrecipient.com
Come speak to me!
Any questions?

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Check recipient - Working for a start-up - why and how

  • 1. Working for Small Companies – Why & How Sabrina Castiglione Chief of Staff Why think about Start-ups? Things to consider when applying to Start-ups What you should do next!
  • 2. CheckRecipient: Working for Small Companies – Why & How WHY THINK ABOUT START-UPS? A career in start-ups isn’t for everyone – but it might be perfect for you! For the right person, small companies can provide a great and stimulating opportunity Here are some factors to consider when thinking about whether a start-up might be the right place for you!
  • 3. CheckRecipient: Working for Small Companies – Why & How WHY THINK ABOUT START-UPS? I want…. More Impact In smaller companies, the effect of your actions is much more visible. Everyone’s a big fish in a small pond! You get to grow something from the ground up! There’s nowhere to hide! At a large company, it’s usually an entire team working together that will influence success. In start-ups, everyone's individual performance matters. That’s a lot of pressure! The flip side… Pressure!
  • 4. CheckRecipient: Working for Small Companies – Why & How WHY THINK ABOUT START-UPS? I want…. Variety In smaller companies, with fewer people, people tend to get stuck in on a broader variety of projects. You won’t be pigeonholed into one activity, and so the work is less repetitive. You won’t have a stable workload and things change on a frequent basis! Scope-creep is common and you’ll often find yourself with a lot on your plate! With such importance placed on every person, start-ups have to be quick to hire and fire. The flip side… Less stability
  • 5. CheckRecipient: Working for Small Companies – Why & How WHY THINK ABOUT START-UPS? I want…. to Learn and Advance - FAST! Start-ups are focused on fast success and fast growth. You’ll take on more than what you were hired on for, probably get to take on multiple positions, and learn two to five times faster than in a corporate position. With fewer people at a start-up, you’re more likely to be promoted if you're doing well Established companies have more developed training programs and give you more ramp-up time. In a start-up, you’re in the deep end from day one… so sink or swim! The flip side… You’re in the deep end!
  • 6. CheckRecipient: Working for Small Companies – Why & How WHY THINK ABOUT START-UPS? I want…. More Autonomy! Generally, there’s less formal structure and bureaucracy in a start-up; with fewer rules, there is more room for creative and entrepreneurial types to express themselves. You get to decide how to do your job! Start-ups lack a structured environment and chaos can sometimes reign! If you find clearly established processes and instructions to be an important comfort, the ‘it doesn’t matter how, find a way to get it done’ attitude might not be for you. The flip side… It can be chaotic!
  • 7. CheckRecipient: Working for Small Companies – Why & How WHY THINK ABOUT START-UPS? I want…. Equity! Start-ups give you a chance to own a piece of what you're working on… and if the company successfully exits, you get to share in the reward. If your start-up is one of the lucky ones – the pay-out can be massive in the end. In the early stages, funds are often low, so established companies generally offer more competitive salaries than early stage start-ups Benefits can be limited until there are more employees, and more funding! The flip side… But that doesn’t happen right away!
  • 8. CheckRecipient: Working for Small Companies – Why & How WHY THINK ABOUT START-UPS? I want…. a Fast-Paced Environment! In large companies, innovation can be slow and results gradual - fruition can take months; In start-ups, results can be immediate and there’s a lot less red tape! Start-ups are dynamic, fast-paced environments that value initiative. And the breadth of work makes them great places to figure out what you excel at. 75% of start-ups fail, and there’s always the chance that your major project could be circumvented by an unanticipated advance, competitor, or invention Additionally, you need to think for yourself, self-teach, and upskill to keep up! The flip side… There’s a risk to that speed!
  • 9. CheckRecipient: Working for Small Companies – Why & How WHY THINK ABOUT START-UPS? I want…. to Believe in Something! Start-ups are mission-driven, and the intense atmosphere can spawn great creativity, innovation, and reward Start-ups are filled with go-getters and people who are willing to go the extra mile With a required level of dedication from everyone that’s rare at a big business, emotions can run high, hours can be long, and work loads can be significant. Start-ups have a small workforce with huge missions, passion about seeing a project through, and every person factors into its success: so it’s not as easy to check out for a while or coast. The flip side… You’re all-in!
  • 10. CheckRecipient: Working for Small Companies – Why & How WHY THINK ABOUT START-UPS? I want…. a Great Culture! Start-ups are fun! Many founders come from stuffy corporate backgrounds and seek to do things differently; a lot of effort is made for teams and workplaces to be social, collegiate, and encouraging. Get a lot of smart, driven people together, and sharing the ups and downs of building a company can be the most fantastic, rewarding experience, and here you can make friends for life! The mission-driven atmosphere also brings people together; If you want to be a part of something, and work with great people, on a great journey with a shared sense of purpose, this is the place to be!
  • 11. CheckRecipient: Working for Small Companies – Why & How ESTABLISHED COMPANIES OR START-UPS? Who are we? What do we do? Why – and how! - you should get to know us! Established Companies Start-Ups Pros Cons Pros Cons More people around you in similar roles to lean on & learn from Impact can be hard to gauge Instant Impact Nowhere to hide Well-defined responsibilities Pigeonholed Repetitive Varied Broader range of activities Less predictable Scope-creep Less predictable Developed training and processes Slower career progression Learn a lot and progress – and fast! In the deep end Structured environment Bureaucratic More autonomy Freedom to define processes Chaotic! Salaries and benefits can be more competitive No ownership in the Company Equity Shoestring budgets! Stable Slow to innovate Fast paced and quick to innovate Riskier! 9-to-5 Can sometimes be ‘just a job’ 9-to-5 Can sometimes be ‘just a job’ Mission driven A lot of personal responsibility Hard work, long hours A lot of personal responsibility Brand-names and recognition Formal feel (although some people prefer this) Great-Culture You work for who?
  • 12. CheckRecipient: Working for Small Companies – Why & How NEXT STEPS Who are we? What do we do? Why – and how! - you should get to know us! Pre application: • Think about what stage of start-up you want to join (1-10 employees? 10-50?) and what kind of model they follow (VC-backed means fast growth and high targets, privately owned are more likely to aim for early profitability and grow slower) • Do your due diligence! Not all start-ups are created equal! • Does the funding come from reputable sources? • What’s the business model? • Who are the competitors? • How is the start-up going to adapt and keep innovating to stay ahead? When applying: • A short but highly relevant and customised cover letter is always preferable to a long but clearly generic one! • Work out the relevant person’s (e.g. CTO) email address and apply directly if you can! • Look at start-up specific job boards and attend start-up specific events & meetups
  • 13. CheckRecipient: Working for Small Companies – Why & How NEXT STEPS Who are we? Interview stage: • Desirable traits to demonstrate (have your competency answers ready!): • Culture is very important; • Show them how you’re a team player! • Demonstrate your individuality and interests! • Demonstrate your adaptability, willingness to learn, and ability to self-teach and multitask! • Show lots of enthusiasm! And be ready to explain why you’re enthused by the opportunity and the mission. • Make it clear that you are willing and able to go the extra mile, and do whatever is needed to get the job done • Show them that you know what you’re getting into, that you have considered the risks and are coming to the opportunity with your eyes open. • Learn the Lingo & about types of funding (e.g. VC-backed) and show that you understand the journey the company is on! Why – and how! - you should get to know us!
  • 14. CheckRecipient: Working for CheckRecipient Find out more! Sabrina Castiglione Chief of Staff CheckRecipient sabrina@checkrecipient.com www.checkrecipient.com checkrecipient.workable.com checkrecipient.com Come speak to me! Any questions?

Editor's Notes

  • #3: Drawbacks of working in a startup generally related to short term risks. Alot to be learned at startups Some people thrive in the sink or swim mentality
  • #4: Est pro: More people around you in similar roles to lean on & learn from Est con: Impact can be hard to gauge SU pro: Instant Impact SU Con: Nowhere to hide Reap the rewards of your personal efforts. EST, you may be the headliner on a project, but people helped or collaborated. SU could be only one on a project, and to see it come to life is rewarding for many people.
  • #5: EST Pro: Well-defined responsibilities Est Con: Pigeonholed, Repetitive SU Pro: Varied, Broader range of activities Less predictable SU Con: Scope-creep, Less predictable EST: v specific job descriptions that limit duties SU: have to adapt from 1 set of duties to another as the startup grows and pivots. mastering new skills, failing for a while, finally doing the new job well" chance to be a part of projects you might not get to touch at another company. Sometimes hi risk hi reward, affect overall success of SU.
  • #6: EST PRO: Developed training and processes EST CON: Slower career progression SU PRO: Learn a lot and progress – and fast! SU CON: In the deep end EST: time to train & acclimate - probably won’t feel the immediate pressure for a few months, if at all. More people to rely on, 1 person won’t make or break the company. SU: even if things go badly, you’ll walk away with an impressive array of new skills.
  • #7: EST PRO: Structured environment EST CON: Bureaucratic SU PRO: More autonomy ,Freedom to define processes SU CON: Chaotic!
  • #8: EST PRO: Salaries and benefits can be more competitive EST CON: No ownership SU Pro: Equity SU Con: Shoestring budgets!
  • #9: EST PRO: Stable EST CON: Slow to innovate SU PRO: Fast paced and quick to innovate SU CON: Riskier! If you want to grow professionally, Sus are the place
  • #10: EST PRO: 9-to-5, Can sometimes be ‘just a job’ EST CON: 9-to-5, Can sometimes be ‘just a job’ SU PRO: Mission driven, A lot of personal responsibility SU CON: Hard work, long hours, A lot of personal responsibility
  • #11: EST PRO: Brand-names and recognition EST CON: Formal feel (although some people prefer this) SU PRO: Great-Culture SU CON: You work for who?
  • #12: Startup companies aren’t for everyone 1 person’s cons may be another person’s pros. Evaluating what you want out of a company, where you see your future, determine the right fit for you. Startups may fail, but always the chance it will be a success even if it isn’t, you will undoubtedly walk away with a unique experience AND A LOT OF NEW SKILLS help you find your next job.  
  • #13: Sabrina, Chief of Staff at CheckRecipient;
  • #14: Sabrina, Chief of Staff at CheckRecipient;